1,2-Dichloroethane → Benzyl {(1S)-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-[(tert-butoxycarbonyl)amino]butyl}carbamate

HRID 269640Notes

Reaction equation

HRID 269640 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:24]([OH:26])=O)[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]([O:31][C:32](=[O:48])[NH:33][CH2:34][CH2:35][CH2:36][C@H:37]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][NH2:39])([CH3:30])([CH3:29])[CH3:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:17]([O:16][C:14](=[O:15])[NH:13][C@H:12]([C:24]([NH:39][CH2:38][C@@H:37]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36][CH2:35][CH2:34][NH:33][C:32]([O:31][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:48])=[O:26])[CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7350734Z-Ndelta-Boc-L-ornithineHCID 57440197HCID 57440197, compound

Product 1

HCID 86624497Benzyl {(1S)-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-[(tert-butoxycarbonyl)amino]butyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation takes place in analogy to Example 79A from 120 mg (0.33 mmol) of N5-(tert-butoxycarbonyl)-N2-[(benzyloxy)carbonyl]-L-ornithine and 136 mg (0.43 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) in 6 ml of dimethylformamide with the addition of 82 mg (0.43 mmol) of EDC and 13 mg (0.1 mmol) of HOBt. The product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→5:95).

Workup

  1. customPreparation
  2. customThe product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→5:95)

Sources & evidence

ORD record
ord-6a5d5f563a0641039e4b732bbdf3c5f7
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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