Acetic Anhydride → (2R,4S)-1-(methanesulfonyloxy)-4-[(2S)-3-methoxy-2-[(2S)-3-methoxy-2-[(2-methyl-1,3-thiazol-5-yl)formamido]propanamido]propanamido]-2-methyl-3-oxo-5-phenylpentan-2-yl acetate

HRID 630602Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][S:9]([O:12][CH2:13][C@:14]([OH:49])([CH3:48])[C:15](=[O:47])[C@@H:16]([NH:24][C:25](=[O:46])[C@@H:26]([NH:30][C:31](=[O:45])[C@@H:32]([NH:36][C:37]([C:39]1[S:43][C:42]([CH3:44])=[N:41][CH:40]=1)=[O:38])[CH2:33][O:34][CH3:35])[CH2:27][O:28][CH3:29])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:11])=[O:10]>>[C:1]([O:49][C@@:14]([CH3:48])([C:15](=[O:47])[C@@H:16]([NH:24][C:25](=[O:46])[C@@H:26]([NH:30][C:31](=[O:45])[C@@H:32]([NH:36][C:37]([C:39]1[S:43][C:42]([CH3:44])=[N:41][CH:40]=1)=[O:38])[CH2:33][O:34][CH3:35])[CH2:27][O:28][CH3:29])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:13][O:12][S:9]([CH3:8])(=[O:10])=[O:11])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 72737659(2R,4S)-2-Hydroxy-4-((S)-3-methoxy-2-((S)-3-methoxy-2-(2-methylthiazole-5-carboxamido)propanamido)propanamido)-2-methyl-3-oxo-5-phenylpentyl methanesulfonate

Product 1

HCID 72737656(2R,4S)-1-(methanesulfonyloxy)-4-[(2S)-3-methoxy-2-[(2S)-3-methoxy-2-[(2-methyl-1,3-thiazol-5-yl)formamido]propanamido]propanamido]-2-methyl-3-oxo-5-phenylpentan-2-yl acetate

Procedure

Prepared according to procedures described above, by reacting acetic anhydride with (2R,4S)-2-hydroxy-4-((S)-3-methoxy-2-((S)-3-methoxy-2-(2-methylthiazole-5-carboxamido)propanamido)propanamido)-2-methyl-3-oxo-5-phenylpentyl methanesulfonate. MS for C28H38N4O11S2 m/z: 671 (M+H)+.

Workup

customPrepared

Sources & evidence

ORD record: ord-875444b15b5e4c0c8050303fc6a922f0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315542B2

Reaction notes

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