(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693556, compound

HRID 575483Notes

Reaction equation

HRID 575483 reaction equation
BrC1C=CC2OCC3(C4SC(C(OCC)=O)=[N:15]C=4C=2C=1)OCCO3.C([C@]1(O)CCN(C)C1=O)#C.[OH:35][C@@:36]1([C:43]#[C:44][C:45]2[CH:67]=[CH:66][C:48]3[O:49][CH2:50][C:51]4([C:56]5[S:60][C:59]([C:61]([O:63]CC)=O)=[N:58][C:57]=5[C:47]=3[CH:46]=2)[O:55][CH2:54][CH2:53][O:52]4)[CH2:40][CH2:39][N:38]([CH3:41])[C:37]1=[O:42]>>[OH:35][C@@:36]1([C:43]#[C:44][C:45]2[CH:67]=[CH:66][C:48]3[O:49][CH2:50][C:51]4([C:56]5[S:60][C:59]([C:61]([NH2:15])=[O:63])=[N:58][C:57]=5[C:47]=3[CH:46]=2)[O:55][CH2:54][CH2:53][O:52]4)[CH2:40][CH2:39][N:38]([CH3:41])[C:37]1=[O:42]

Participants

4

Reactant 3

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693557HCID 86693557, compoundHCID 86693558HCID 86693558, compound

Product 1

HCID 86693556HCID 86693556, compound

Procedure

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

Workup

  1. customto give

Sources & evidence

ORD record
ord-6accfa059e7e47c4b1ba51dfba9d4102
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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