Isobutyl chloroformate → 7-(hydroxymethyl)-1H-pyrido[2,3-b][1,4]thiazin-2(3H)-one

HRID 1435862Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][S:6][C:5]2[N:8]=[CH:9][C:10]([C:12](O)=[O:13])=[CH:11][C:4]=2[NH:3]1.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>>[OH:13][CH2:12][C:10]1[CH:9]=[N:8][C:5]2[S:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=2[CH:11]=1

Participants

Reactant 3

HCID 62365Isobutyl chloroformate

HCID 4311764Sodium borohydride

HCID 218736922,3-Dihydro-2-oxo-1H-pyrido[2,3-b][1,4]thiazine-7-carboxylic acid

Product 1

HCID 218737287-(hydroxymethyl)-1H-pyrido[2,3-b][1,4]thiazin-2(3H)-oneYield 56.2%

Procedure

2-Oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-7-carboxylic acid (2.48 g) was reacted with iso-butylchloroformate and sodium borohydride by the method of Preparation (14b) to afford a solid (1.3 g), after recrystallisation from chloroform-methanol (9:1). MS (ES) m/e 197 (M+H)+.

Sources & evidence

ORD record: ord-43de51b122d34dc28ddbfadd8580d79f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618959B2

Reaction notes

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