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

HRID 269646Notes

Reaction equation

HRID 269646 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21](=[O:37])[NH:22][CH2:23][CH2:24][CH2:25][C@H:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][NH2:28])([CH3:19])([CH3:18])[CH3:17].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C:13]([NH:28][CH2:27][C@@H:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][CH2:24][CH2:23][NH:22][C:21]([O:20][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:37])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14349BenzyloxycarbonylglycineHCID 757711-HydroxybenzotriazoleHCID 57440197tert-Butyl {(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Product 1

HCID 86624495Benzyl [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 92 mg (0.44 mmol) of N-[(benzyloxy)carbonyl]glycine and 181 mg (0.57 mmol) of tert-butyl{(4S)-5-amino-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate (Example 86A) in 6 ml of dimethylformamide with the addition of 110 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-ee14f4180ce248a384c03344bb2320af
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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