Hydrochloric Acid → Z-Val-Pro-Val-Pro-CH2-Cl

HRID 1821561Notes

Reaction equation

HRID 1821561 reaction equation
[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:6]([N:8]1[CH2:29][CH2:28][CH2:27][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21](O)=[O:22])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH3:40]N1CCOCC1.[N+](=C)=[N-].[ClH:50]>O1CCOCC1>[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:6]([N:8]1[CH2:29][CH2:28][CH2:27][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([CH2:40][Cl:50])=[O:22])=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 9550DiazomethaneHCID 131727672Z-Val-Pro-Val-Pro-OH

Product 1

HCID 131727671Z-Val-Pro-Val-Pro-CH2-Cl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10 (1.1 g, 2.01 mmol) was treated as described for 13 using CAIBE (0.263 ml, 2.01 mmol), NMM (0.223 ml, 2.02 mmol), diazomethane (10 mmol in 13.3 ml ether) and 5 ml of HCl in dioxane (7.6M).

Sources & evidence

ORD record
ord-423cddb29ec3498a9ef654a0fc898dce
Source dataset
uspto-grants-2009_10
Patent number
US07608577B2

Reaction notes

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