Diisopropylethylamine → HCID 178450011, compound

HRID 333408Notes

Reaction equation

HRID 333408 reaction equation
[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:3]([N:5]1[CH2:10][CH2:9][C:8]([C:17](=[O:21])[CH2:18][CH2:19][CH3:20])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C(N(C(C)C)CC)(C)C.Cl[C:41](OC1C=CC([N+]([O-])=O)=CC=1)=[O:42].Cl.Cl.[NH2:55][CH2:56][CH2:57][C:58]1[N:62]=[CH:61][NH:60][CH:59]=1>ClCCl.CN(C)C=O>[C:17]([C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C@@H:2]([NH:1][C:41]([NH:55][CH2:56][CH2:57][C:58]2[N:62]=[CH:61][NH:60][CH:59]=2)=[O:42])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH2:6][CH2:7]1)(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 66987881HCID 66987881, compoundHCID 178478691HCID 178478691, compound

Product 1

HCID 178450011HCID 178450011, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 100 mg (0.245 mmol) of 1-{1-[(S)-2-amino-3-(4-methoxy-phenyl)propionyl]-4-phenylpiperidin-4-yl}butan-1-one in 10 mL of dichloromethane are added 64 μL of diisopropylethylamine and then 74 mg (0.368 mmol) of 4-nitrophenyl chloroformate. The medium is stirred at room temperature for 1 hour 30 minutes. A solution containing 90 mg (0.489 mmol) of histamine dihydrochloride and 0.15 mL of diisopropylethylamine in 5 mL of dichloromethane and 2 mL of dimethylformamide is added to this mixture.

Workup

  1. additionis added to this mixture

Sources & evidence

ORD record
ord-9a6a3ac2ff664702aa71e42cef1a9398
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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