Diisopropylethylamine → 2-{3-[(1R,2R)-2-butoxycarbonyl-1-(2-chloro-benzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic acid

HRID 2361115Notes

Reaction equation

HRID 2361115 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([OH:3])=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:49]([O:53][C:54](=[O:67])[C@H:55]([OH:66])[C@H:56]([NH2:65])[CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[Cl:64])[CH2:50][CH2:51][CH3:52]>C(Cl)Cl>[CH2:49]([O:53][C:54]([C@H:55]([OH:66])[C@H:56]([NH:65][C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:3])[CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[Cl:64])=[O:67])[CH2:50][CH2:51][CH3:52]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 124220832-(3-Carboxypropyl)benzoic acidHCID 71073857(2R,3R)-3-amino-4-(2-chloro-phenyl)-2-hydroxy-butyric Acid Butyl Ester

Product 1

HCID 710736552-{3-[(1R,2R)-2-butoxycarbonyl-1-(2-chloro-benzyl)-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Carboxy-propyl)benzoic acid (300 mg, 1.4 mmol, 1.0 eq.) was combined with DIPEA (803 μL, 3.2 eq.) and HATU (548 mg, 1.4 mmol, 1.0 eq.) in DCM (30 mL). The mixture was stirred for 10 min and (2R,3R)-3-amino-4-(2-chloro-phenyl)-2-hydroxy-butyric acid butyl ester (412 mg, 1.4 mmol, 1.0 eq.) was added. The reaction was quenched after 1 hour by adding saturated NH4Cl and the product was extracted with DCM, dried and evaporated. AcOH (1 mL) was added and the resulting product was purified by preparative HPLC to yield the title compound (260 mg, 99% purity). MS m/z [M+H]+ calc'd for C25H30ClNO6, 476.18. found 476.2.

Workup

  1. customThe reaction was quenched after 1 hour
  2. additionby adding saturated NH4Cl
  3. extractionthe product was extracted with DCM
  4. customdried
  5. customevaporated
  6. additionAcOH (1 mL) was added
  7. customthe resulting product was purified by preparative HPLC

Sources & evidence

ORD record
ord-35a20dfe39e9482c803a5bb9c73d927a
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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