4-Pentenoic acid → HCID 56611441, compound

HRID 375759Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:13][O:12][C:11](=[O:14])[C:10]2[CH:15]=[C:16]([O:27][CH3:28])[CH:17]=[C:18]([O:19][Si](C(C)(C)C)(C)C)[C:9]=2[CH2:8][S:7][CH2:6][C@@H:5]([C:29]([O:31][CH3:32])=[O:30])[NH:4][C:3]1=[O:33].[CH2:34]([CH2:37][C:38](O)=[O:39])[CH:35]=[CH2:36]>>[C:38]([NH:1][C@H:2]1[CH2:13][O:12][C:11](=[O:14])[C:10]2[CH:15]=[C:16]([O:27][CH3:28])[CH:17]=[C:18]([OH:19])[C:9]=2[CH2:8][S:7][CH2:6][C@@H:5]([C:29]([O:31][CH3:32])=[O:30])[NH:4][C:3]1=[O:33])(=[O:39])[CH2:37][CH2:34][CH:35]=[CH2:36]

Participants

Reactant 2

HCID 611384-Pentenoic acid

HCID 54142415HCID 54142415, compound

Product 1

HCID 56611441HCID 56611441, compound

Procedure

Methyl (4R, 7S)-7-amino-14-(tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-12-methoxy-6,10-dioxo-9,2,5-benzoxathiaazacyciododecine-4-carboxylate was acylated with allylacetic acid in an analogues manner as described in Example 122 and the protection groups were subsequently cleaved off using the procedure described in Example 13 to yield methyl (4R,7S)-7-(pent-4-enoylamino)-1,3,4,5,6,7,8,10-octahydro-14-hydroxy-12-methoxy-6,10-dioxo-9,2,5-benzooxathiaazacyclododecine-4-carboxylate as a white solid.

Sources & evidence

ORD record: ord-5cdce3f9b1994d939704cdba36594c18
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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