1,2-Dichloroethane → N2-(tert-butoxycarbonyl)-N1-[(1S)-1-({[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]amino}carbonyl)propyl]-4-methyl-D-leucinamide

HRID 857805Notes

Reaction equation

HRID 857805 reaction equation
[C:1]([NH:8][C@@H:9]([C:15]([OH:17])=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:18][C@@H:19]([CH2:36][CH3:37])[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[O:21].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CO>[C:4]([O:3][C:1]([NH:8][C@@H:9]([C:15]([NH:18][C@H:19]([C:20]([NH:22][CH2:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[O:21])[CH2:36][CH3:37])=[O:17])[CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 7021114(R)-2-((tert-Butoxycarbonyl)amino)-4,4-dimethylpentanoic acidHCID 69656288(2S)-2-amino-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]butanamide

Product 1

HCID 86591819N2-(tert-butoxycarbonyl)-N1-[(1S)-1-({[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]amino}carbonyl)propyl]-4-methyl-D-leucinamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Boc-D-t-butyl-alanine (49 mg, 0.20 mmol), (2S)-2-amino-N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]butanamide (66 mg, 0.20 mg), HOAt (27 mg, 0.20 mmol), EDC (57 mg, 0.30 mmol), and Et3N (28 μL, 0.20 mmol) in 1.0 mL of DMF was stirred at rt overnight. A small amount of MeOH was used to aid in dissolution. Solvent was removed in vacuo to give the title compound, which was carried on directly to deprotection. LCMS (M+H): 521.2.

Workup

  1. dissolutionto aid in dissolution
  2. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-aefaf23bf3594c7fa2b416bf9873282f
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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