1,2-Dichloroethane → Benzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate

HRID 269648Notes

Reaction equation

HRID 269648 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:22]([OH:24])=O)[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O:29][C:30](=[O:46])[NH:31][CH2:32][CH2:33][CH2:34][C@H:35]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36][NH2:37])([CH3:28])([CH3:27])[CH3:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:15]([O:14][C:12](=[O:13])[NH:11][C@@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:22]([NH:37][CH2:36][C@@H:35]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34][CH2:33][CH2:32][NH:31][C:30]([O:29][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:46])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6993425N-((Phenylmethoxy)carbonyl)-O-(phenylmethyl)-L-serineHCID 57440197tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Product 1

HCID 86624498Benzyl [(1S)-1-[(benzyloxy)methyl]-2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation takes place in analogy to Example 79A from 150 mg (0.46 mmol) of O-benzyl-N-[(benzyloxy)carbonyl]-L-serine and 188 mg (0.59 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) in 6 ml of dimethylformamide with the addition of 114 mg (0.57 mmol) of EDC and 18 mg (0.13 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-fde0cb4cf4fd40a09c776538310135cc
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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