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Benzylamine → ((S)-1-benzylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

HRID 1707330
Notes
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Reaction equation

HRID 1707330 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:36]([NH:43][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 7201376((S)-1-benzylcarbamoyl-ethyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-t-Butoxycarbonyl-L-alanine (377 mg, 2.0 mmol), HOBT (283 mg, 2.1 mmol) and EDC hydrochloride (420 mg, 2.2 mmol) were dissolved in 5 mL of DMF. Benzylamine (230 μL, 2.1 mmol) was added followed by triethylamine (280 μL, 1.9 mmol). The mixture was stirred overnight and the solvent was evaporated. The residue was partitioned between ethyl acetate and 10% citric acid and the organic phase was washed sequentially with 10% sodium bicarbonate and brine. The solution was dried and evaporated to yield 498 mg of a waxy solid.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was partitioned between ethyl acetate and 10% citric acid
  3. washthe organic phase was washed sequentially with 10% sodium bicarbonate and brine
  4. customThe solution was dried
  5. customevaporated
  6. customto yield 498 mg of a waxy solid

Sources & evidence

ORD record
ord-27e4111bc2294ea7b1dad014b6490c62
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05352705

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes