1,2-Dichloroethane → HCID 131727148, compound

HRID 269620Notes

Reaction equation

HRID 269620 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][C@H:29]([CH2:40][OH:41])[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:24]([NH:28][C@H:29]([CH2:40][OH:41])[CH2:30][CH2:31][NH:32][C:33]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:39])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 57463635HCID 57463635, compound

Product 1

HCID 131727148HCID 131727148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation takes place in analogy to Example 79A from 140 mg (0.38 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine and 120 mg (0.50 mmol) of tert-butyl [(3S)-3-amino-4-hydroxybutyl]carbamate hydrochloride (Example 88A) in 6 ml of dimethylformamide with the addition of 96 mg (0.50 mmol) of EDC, 16 mg (0.12 mmol) of HOBt and 0.17 ml (1.00 mmol) of diisopropylethylamine. The product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→10:90).

Workup

  1. customPreparation
  2. customThe product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→10:90)

Sources & evidence

ORD record
ord-d87cf6018eae4e56837cff4462dc92be
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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