Methoxyacetyl chloride → HCID 69783003, compound

HRID 1291795Notes

Reaction equation

HRID 1291795 reaction equation
[OH:1][C@H:2]([C@@H:24]([NH:32][C:33](=[O:43])[C@H:34]([CH:40]([CH3:42])[CH3:41])[NH:35][C:36]([O:38][CH3:39])=[O:37])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:3][N:4]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[NH:5][C:6](=[O:16])[C@H:7]([CH:13]([CH3:15])[CH3:14])[NH:8][C:9]([O:11][CH3:12])=[O:10].[CH3:44][O:45][CH2:46][C:47](Cl)=[O:48]>O1CCOCC1.N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:44][O:45][CH2:46][C:47]([O:1][C@H:2]([C@@H:24]([NH:32][C:33](=[O:43])[C@H:34]([CH:40]([CH3:42])[CH3:41])[NH:35][C:36]([O:38][CH3:39])=[O:37])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:3][N:4]([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[NH:5][C:6](=[O:16])[C@H:7]([CH:13]([CH3:14])[CH3:15])[NH:8][C:9]([O:11][CH3:12])=[O:10])=[O:48]

Participants

6

Reactant 2

HCID 96623Methoxyacetyl chloride2×HCID 461993methyl N-[(1S)-1-[[(1S,2S)-1-benzyl-3-[cyclohexylmethyl-[[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]amino]amino]-2-hydroxy-propyl]carbamoyl]-2-methyl-propyl]carbamate

Product 1

HCID 69783003HCID 69783003, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

Analogously to Example 105, 200 mg (0.33 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(methoxycarbonyl)-(L)-valyl)amino-4-phenyl-butyl]-1-[cyclohexylmethyl]-2-[N-methoxycarbonyl-(L)-valyl]-hydrazine (Example 73a) in 2.6 ml of dioxane and 0.4 ml of pyridine are reacted with 50 μl (0.495 mmol) of methoxyacetic acid chloride and 2 mg (0.017 mmol) of DMAP. To complete the reaction a further 0.5 equivalents of methoxyacetic acid chloride and a few granules of DMAP are added and the mixture is stirred. Extraction and digestion from DIPE/hexane in an ultrasound bath yields the pure title compound: TLC Rf (O)=0.48; tRet (V)=15.6 min; FAB-MS (M+H)+ =678.

Workup

  1. extractionExtraction and digestion from DIPE/hexane in an ultrasound bath

Sources & evidence

ORD record
ord-593f93e0dcc44148a6e892b9ed0bda1d
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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