Benzyloxycarbonylglycine → HCID 69284585, compound

HRID 2225261Notes

Reaction equation

HRID 2225261 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C@H:3]1[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH2:25]([O:32][C:33]([NH:35][CH2:36][C:37](O)=[O:38])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:25]([O:32][C:33]([NH:35][CH2:36][C:37]([NH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:4][C@H:3]1[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:38])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69284626HCID 69284626, compound

Product 1

HCID 69284585HCID 69284585, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyl 3-((1R,2S,5R)-2-amino-5-(tert-butoxycarbonylamino)cyclohexyl)propanoate (90 mg) and 2-(benzyloxycarbonylamino)acetic acid (55 mg) in dichloromethane (2 mL) was treated sequentially with diisopropylethylamine (92 μL), 1-hydroxybenzotriazole hydrate (45 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (61 mg). The mixture was stirred at rt for 20 h, then was diluted with dichloromethane, washed sequentially with 1 M aqueous HCl, saturated aqueous NaHCO3 and water, dried over Na2SO4 and concentrated under vacuum to provide tert-butyl 3-((1R,2S,5R)-2-(2-(benzyloxycarbonylamino)acetamido)-5-(tert-butoxycarbonylamino)cyclohexyl)propanoate as a pale yellow gum (125 mg). MS found: (M+H)+=534.5.

Workup

  1. washwashed sequentially with 1 M aqueous HCl, saturated aqueous NaHCO3 and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1be1d35728f6408db92deaa782aa588c
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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