1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

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Basic information

CAS: 64187-48-0
Standard SMILES: COC(=O)C1CC(O)CN1C(=O)OCc1ccccc1
InChIKey: VVKAGQHUUDRPOI-UHFFFAOYSA-N
Molecular formula: C14H17NO5
Average molar mass: 279.29 g/mol
Monoisotopic mass: 279.11067264

Names & identifiers

Preferred name: 1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
IUPAC: 1-O-benzyl 2-O-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate
English name: Z-Hyp-OMe
Molecular formula: C14H17NO5
Molecular weight: 279.29

Names & synonyms

1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate92246-88-3N-Cbz-L-4-Hydroxyproline methyl esterNSC293847SCHEMBL636507DTXSID30982724AKOS023599747NSC-293847PB26538PB32108SB18510Z-L-trans-4-hydroxyproline methyl ester

Show more names

1-Benzyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylateCBZ-Hyp-OMe(2S,4R)-1-Benzyl 2-Methyl 4-hydroxypyrrolidine-1,2-dicarboxylateO1-benzyl O2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylateZ-Hyp-OMeZ-L-Hyp-OMeCbz-L-Hyp-OMeCbz-Hyp-Ome-OHZ-Hyp-OMe (Syrup)Z-HYP-OME USP/EP/BP

LS-14303EN300-2974061-benzyl2-methyl4-hydroxypyrrolidine-1,2-dicarboxylateO1-benzyl O2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Database identifiers

CAS: 64187-48-0
PubChem CID: 325313
DTXSID: DTXSID30982724
Nikkaji: J1.530.449I

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 76.1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 20
Formal charge: 0
Complexity: 353

Physicochemical properties

Boiling point: 422.8 · 422.8±45.0 °C(Predicted)
Density: 1.313 · 1.313
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
pka: 14.25 · 14.25±0.40(Predicted)
form: viscous liquid
color: Pale yellow
optical activity: Consistent with structure
InChI: InChI=1S/C14H17NO5/c1-19-13(17)12-7-11(16)8-15(12)14(18)20-9-10-5-3-2-4-6-10/h2-6,11-12,16H,7-9H2,1H3/t11-,12+/m1/s1
InChIKey: VVKAGQHUUDRPOI-NEPJUHHUSA-N
SMILES: N1(C(OCC2=CC=CC=C2)=O)C[C@H](O)C[C@H]1C(OC)=O
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk: 3
hs_code: 2933.99.8290
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Chemistry & industry

Applications

UsesN-(Benzyloxycarbonyl)-4-hydroxyproline Methyl Ester, can be used as an intermediate in the synthesis of various pharmaceutical and biologically active compounds. It is used in the synthesis of Doripenem (D534800), an Antibacterial agent.

Upstream & downstream products

Downstream products

2-PyrrolidineMethanol, 4-hydroxy-, hydrochloride (1:1), (2S,4R)-N-BOC-cis-4-fluoro-L-proline Carbamic acid, [[(2S,4R)-4-hydroxy-2-pyrrolidinyl]methyl]-, 1,1-dimethylethyl Carbamic acid, [(3S,5S)-5-(hydroxymethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl 3-Pyrrolidinol, 5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-, (3R,5S)-Z-trans-4-hydroxy-L-prolinol

Related reactions

7 records

New reaction record

HRID 110412As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

HRID 688639As productTraining data from https://doi.org/10.1039/C8SC04228D (3/10)

HRID 822732As reactantTest data from https://doi.org/10.1039/C8SC04228D

HRID 823419As productTest data from https://doi.org/10.1039/C8SC04228D

HRID 958440As reactantValidation data from https://doi.org/10.1039/C8SC04228D

HRID 1202049As reactantTraining data from https://doi.org/10.1039/C8SC04228D (5/10)

HRID 2157160As reactantTraining data from https://doi.org/10.1039/C8SC04228D (4/10)

Compound notes

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