(2S)-2-t-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanal → (2R)-2-t-Butoxycarbonylamino-2-ethyl-1-n-hexanoyloxy-4-(1-methylpyrrol-2-yl)-3-butene

HRID 604554Notes

Reaction equation

HRID 604554 reaction equation
[I-].[CH3:2][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:28]([O:32][C:33]([NH:35][C@@:36]([CH2:48][CH3:49])([CH2:39][O:40][C:41](=[O:47])[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:37]=O)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([NH:35][C@:36]([CH2:48][CH3:49])([CH:37]=[CH:8][C:4]1[N:3]([CH3:2])[CH:7]=[CH:6][CH:5]=1)[CH2:39][O:40][C:41](=[O:47])[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:34])([CH3:30])([CH3:31])[CH3:29]

Participants

3

Reactant 2

HCID 20721240(2S)-2-t-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanalHCID 23031470(1-Methylpyrrol-2-yl)methyltriphenylphosphonium iodide

Product 1

HCID 67040419(2R)-2-t-Butoxycarbonylamino-2-ethyl-1-n-hexanoyloxy-4-(1-methylpyrrol-2-yl)-3-buteneYield 69%

Procedure

The reaction was carried out in the similar manner to Reference example 1 (1d) using (1-methylpyrrol-2-yl)methyltriphenylphosphonium iodide obtained in Reference example 1 (1c) and (2S)-2-t-butoxycarbonylamino-3-n-hexanoyloxy-2-ethyl-1-propanal obtained in Reference example 2 (2b) as starting materials to obtain the title compound (yield: 69%).

Sources & evidence

ORD record
ord-0c3a2e4a834b465d80ec99d884eac3be
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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