1,2-Dichloroethane → Benzyl[2-({(2s)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}amino)ethyl]carbamate

HRID 269642Notes

Reaction equation

HRID 269642 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:24]([OH:26])=O)[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:34]([O:33][C:32](=[O:41])[NH:31][CH2:30][CH2:29][NH:28][C:24](=[O:26])[C@@H:15]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochloride

Product 1

HCID 131727156Benzyl[2-({(2s)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}amino)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation takes place in analogy to Example 79A from 300 mg (0.82 mmol) of N5-[(benzyloxy)carbonyl]-N-(tert-butoxycarbonyl)-L-ornithine and 246 mg (1.06 mmol) of benzyl (2-aminoethyl)carbamate hydrochloride in 6 ml of dimethylformamide with the addition of 204 mg (1.06 mmol) of EDC, 33 mg (0.25 mmol) of HOBt and 148 mg (1.15 mmol) of N,N-diisopropylethylamine.

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-e856a93f80f14b63b9ac5a853cc27810
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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