1,2-Dichloroethane → benzyl{(1S)-3-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]propyl}carbamate

HRID 269624Notes

Reaction equation

HRID 269624 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH:34]([OH:37])[CH2:35][NH2:36])([CH3:29])([CH3:28])[CH3:27].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:13]([NH:36][CH2:35][CH:34]([OH:37])[CH2:33][NH:32][C:31]([O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:38])=[O:15])[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7019789(S)-2-(((Benzyloxy)carbonyl)amino)-4-((tert-butoxycarbonyl)amino)butanoic acidHCID 10511887tert-butyl N-(3-amino-2-hydroxypropyl)carbamate

Product 1

HCID 131727150benzyl{(1S)-3-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]propyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

44 mg (0.12 mmol) of the compound from Example 97A and 40 mg (0.21 mmol) of tert-butyl(3-amino-2-hydroxypropyl)carbamate are dissolved in 1 ml of DMF and cooled to 0° C., and 40.3 mg (0.21 mmol) of EDC and 5.51 mg (0.04 mmol) of HOBt are successively added. The mixture is allowed to warm to room temperature and is stirred overnight. After concentration in vacuo, purification by chromatography on silica gel (dichloromethane/methanol 20:1) results in the title compound.

Workup

  1. temperatureto warm to room temperature
  2. concentrationAfter concentration
  3. customin vacuo, purification by chromatography on silica gel (dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-7e20b9c9056f40c2be3c2d09c4273fed
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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