HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxypropyl)cyclopropanecarboxylate

HRID 1967277
Notes
Print preview

Reaction equation

HRID 1967277 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:25])[C:13]([C:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:25])[CH:13]([C:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)[OH:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59556932HCID 59556932, compound

Product 1

HCID 59556880tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxypropyl)cyclopropanecarboxylateYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}propanoyl)cyclopropanecarboxylate (1.66 g) in methanol (25 mL) was cooled to 0° C., 90% sodium borohydride (305 mg) was added, and the mixture was stirred at 0° C. for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/1) to give the title compound as a colorless oil (yield: 1.58 g, 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/1)

Sources & evidence

ORD record
ord-a90a042fa83e411eac1b298d962e86e0
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420694B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes