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

HRID 857807Notes

Reaction equation

HRID 857807 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][N: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][N: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 69656202(2S)-2-amino-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]butanamide

Product 1

HCID 86591820N2-(tert-butoxycarbonyl)-N1-[(1S)-1-({[5-chloro-2-(1H-tetraazol-1-yl)benzyl]amino}carbonyl)propyl]-4-methyl-D-leucinamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Boc-D-tert-butyl-alanine (74 mg, 0.30 mmol), (2S)-2-amino-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]butanamide (99 mg, 0.30 mmol), HOAt (41 mg, 0.30 mmol), EDC (86 mg, 0.45 mmol), and Et3N (42 μL, 0.30 mmol) in DMF (1.0 mL) was stirred at rt overnight. A small amount of MeOH was added to aid in dissolution. Solvent was removed in vacuo to give the title compound, which was carried on directly to deprotection. LCMS (M+H): 522.0.

Workup

  1. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-acd2cd67f787479b926c206881182763
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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