(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693412, compound

HRID 575368Notes

Reaction equation

HRID 575368 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH2:14][CH:13]([OH:16])[C:12]3[S:11][C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:9][C:8]=3[C:6]=2[CH:7]=1.[C:21]([C@:23]1([OH:30])[CH2:27][CH2:26][N:25]([CH3:28])[C:24]1=[O:29])#[CH:22]>>[OH:16][CH:13]1[C:12]2[S:11][C:10]([C:17]([O:19][CH3:20])=[O:18])=[N:9][C:8]=2[C:6]2[CH:7]=[C:2]([C:22]#[C:21][C@:23]3([OH:30])[CH2:27][CH2:26][N:25]([CH3:28])[C:24]3=[O:29])[CH:3]=[CH:4][C:5]=2[O:15][CH2:14]1

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693413HCID 86693413, compound

Product 1

HCID 86693412HCID 86693412, compound

Procedure

Methyl 9-bromo-4-oxo-[1]benzoxepino[5,4-d]thiazole-2-carboxylate (0.37 g) was subjected to General Procedure 0 to afford 280 mg (75%) of methyl 9-bromo-4-hydroxy-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate. Methyl 9-bromo-4-hydroxy-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate (128 mg) was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one similarly to as described in General Procedure F with non-critical modifications to afford methyl 4-hydroxy-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate which was directed subjected to General Procedure M to afford 25 mg and 7.9 mg (26% overall yield) after reverse phase purification then chiral separation. The absolute stereochemistry at the 4-hydroxyl substitution position for each isomer was not determined.

Sources & evidence

ORD record
ord-46146a5d141b48beab0e47ba4b217990
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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