Sodium 2-mercaptobenzothiazole → 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-((benzo[d]thiazol-2-ylthio)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

HRID 39405Notes

Reaction equation

HRID 39405 reaction equation
Cl[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:24])([CH3:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])[CH2:4]1.[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[S-:34].[Na+]>>[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[S:34][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:24])([CH3:23])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:13])[CH2:4]1

Participants

3

Reactant 2

HCID 3714831Sodium 2-mercaptobenzothiazoleHCID 676077022-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Product 1

HCID 676072292-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-((benzo[d]thiazol-2-ylthio)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Procedure

The procedure was carried out in the same manner as in Example 11, except that 3.5 g of 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate was used in place of 30 g thereof, and sodium benzo[d]thiazole-2-thiolate (3.8 g) prepared in Example 10 was used in place of sodium 1-phenyl-1H-tetrazole-5-thiolate. The title compound was obtained (4.6 g).

Sources & evidence

ORD record
ord-61796bcabce2467a915e2d5d5e14604a
Source dataset
uspto-grants-2013_09
Patent number
US08524914B2

Reaction notes

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