1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

HRID 1677062Notes

Reaction equation

HRID 1677062 reaction equation
C([N:4]([CH2:8]C)C(C)C)(C)C.Cl.CN[O:13][CH3:14].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:36]([O:43][C@H:44]([CH3:60])[C@H:45]([NH:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:46][O:47][CH2:48][C:49]([OH:51])=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[C:56]([O:55][C:53](=[O:54])[NH:52][C@H:45]([CH2:46][O:47][CH2:48][C:49](=[O:51])[NH:4][CH2:8][O:13][CH3:14])[C@H:44]([O:43][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH3:60])([CH3:59])([CH3:58])[CH3:57]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 67373378((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid

Product 1

HCID 67379173{(1R,2R)-2-benzyloxy-1-[(methoxymethylcarbamoyl)methoxymethyl]propyl}carbamic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-diisopropylethylamine (41 mL), N,O-dimethylhydroxyamine hydrochloride (17.4 g), EDCI (34.3 g), HOBt (24.1 g) were added in sequence to a DMF (400 mL) solution of ((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid (42.1 g), and stirring was continued for 16 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and water were added, and the organic layer was partitioned. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. After passing the residue through a silica pad (silica gel 500 cc), the solvent was removed under a vacuum, and the title compound (46.0 g) was obtained. The physical property values are as follows.

Workup

  1. customThe solvent was removed under a vacuum, and ethyl acetate and water
  2. additionwere added
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under a vacuum
  7. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-1571651a168b4fa891512bfbd26d277b
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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