1-Hydroxybenzotriazole → HCID 86618164, compound

HRID 2246607Notes

Reaction equation

HRID 2246607 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([O:8][CH3:9])[CH2:4][C@H:3]1[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].ON1C2C=CC=CC=2N=N1.[C:29]([NH:39][C@H:40]([C:45](O)=[O:46])[CH2:41][CH2:42][S:43][CH3:44])([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O>[CH2:32]([O:31][C:29]([NH:39][C@@H:40]([CH2:41][CH2:42][S:43][CH3:44])[C:45]([NH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([O:8][CH3:9])[CH2:4][C@H:3]1[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:46])=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1550857Benzyloxycarbonyl-L-methionineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86618165HCID 86618165, compound

Product 1

HCID 86618164HCID 86618164, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A sample of tert-butyl ((1S,2S,5R)-2-amino-5-methoxycyclohexyl)methylcarbamate (2.53 g, 9.79 mmol) was dissolved in CH2Cl2 (50 ml) at room temperature. The solution was charged sequentially with 1-hydroxybenzotriazole (1.456 g, 10.77 mmol), N-carbobenzyloxy-L-methionine (4.16 g, 14.69 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.440 g, 12.73 mmol). The reaction mixture was stirred overnight. It was diluted with EtOAc and washed with saturated Na2CO3, followed by brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo to yield tert-butyl ((1S,2S,5R)-2-((S)-2-benzyloxycarbonylamino-4-(methylthio)butanamido)-5-methoxycyclohexyl)methylcarbamate as a colorless sticky solid. LC/MS found [M+H]+=524.31.

Workup

  1. washwashed with saturated Na2CO3
  2. dry with materialThe solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f435e3294c646a3969d132c16fd7c6b
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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