Acetic Anhydride → HCID 53378461, compound

HRID 1620429Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:13]2[CH2:18][CH2:17][CH:16]3[S:19][C:20](=[O:22])[CH:21]=[C:15]3[CH2:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].ClC1C=CC(CC([O-])=O)=CC=1>>[C:23]([O:22][C:20]1[S:19][C:16]2[CH2:17][CH2:18][N:13]([C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9]([O:11][CH3:12])=[O:10])[CH2:14][C:15]=2[CH:21]=1)(=[O:25])[CH3:24]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 5460378HCID 5460378, compound

HCID 68264123HCID 68264123, compound

Product 1

HCID 53378461HCID 53378461, compoundYield 97%

Procedure

Following the method described in Example 4, (2S)-methyl 2-(4-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3.2-c]pyridin-5 (2H,4H,6H)-yl)-acetate (IV-3) (100 mg) was reacted with acetic anhydride (63 μl), to prepare (S)-methyl 2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(4-chlorophenyl-acetate (I-20) (110 mg). Yield 97%. 1H-NMR (300 MHz, CDCl3) δ 2.27 (s, 3H), 2.65-2.78 (m, 4H), 3.53 (s, 2H), 3.73 (s, 3H), 4.30 (s, 1H), 6.25 (s, 1H), 7.33-7.46 (m, 4H); 13C-NMR (75 MHz, CDCl3) δ 20.7, 24.7, 48.1, 50.4, 52.2, 71.9, 111.9, 125.7, 128.9, 130.1, 134.3, 134.4, 149.6, 167.7, 171.4; ESI-MS m/z 380.1 [M+H]+; HRMS Calcd for C18H19NO4SCl [M+H]+ m/z 380.0723. found 380.0735.

Sources & evidence

ORD record: ord-cecafd80848141b8ac13a03ce2fe8f58
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772489B2

Reaction notes

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