(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693554, compound

HRID 575482Notes

Reaction equation

HRID 575482 reaction equation
BrC1C(F)=CC2OCC(F)C3SC(C(OCC)=O)=[N:11]C=3C=2C=1.C([C@]1(O)CCN(C)C1=O)#C.[F:33][CH:34]1[C:43]2[S:42][C:41]([C:44]([O:46]CC)=O)=[N:40][C:39]=2[C:38]2[CH:49]=[C:50]([C:54]#[C:55][C@:56]3([OH:63])[CH2:60][CH2:59][N:58]([CH3:61])[C:57]3=[O:62])[C:51]([F:53])=[CH:52][C:37]=2[O:36][CH2:35]1>>[F:33][CH:34]1[C:43]2[S:42][C:41]([C:44]([NH2:11])=[O:46])=[N:40][C:39]=2[C:38]2[CH:49]=[C:50]([C:54]#[C:55][C@:56]3([OH:63])[CH2:60][CH2:59][N:58]([CH3:61])[C:57]3=[O:62])[C:51]([F:53])=[CH:52][C:37]=2[O:36][CH2:35]1

Participants

4

Reactant 3

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693555HCID 86693555, compoundHCID 89754422HCID 89754422, compound

Product 1

HCID 86693554HCID 86693554, compound

Procedure

Similar to as described in General Procedure G, racemic ethyl 9-bromo-4,8-difluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate was reacted with (R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one to give a diasteromeric mixture of ethyl 4,8-difluoro-9-(((R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate. Following aminolysis of the ethyl ester (similar to as described in General Procedure M) a diasteromeric mixture of the titled compounds was obtained after purification by prep HPLC.

Workup

  1. customto give
  2. customwas obtained
  3. customafter purification by prep HPLC

Sources & evidence

ORD record
ord-f66fce16e73f4ef68672ef63049836f1
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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