HCID 86762147, compound → HCID 86762148, compound

HRID 1907410Notes

Reaction equation

HRID 1907410 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([F:27])=[C:8]([C@:10]23[O:18][CH2:17][CH2:16][C@H:15]2[CH2:14][S:13][C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[N:11]3)[CH:9]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([F:27])=[C:8]([C@@:10]23[O:18][CH2:17][CH2:16][C@@H:15]2[CH2:14][S:13][C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[N:11]3)[CH:9]=1

Participants

4

Reactant 1

HCID 86762147HCID 86762147, compound

Product 1

HCID 86762148HCID 86762148, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of tert-butyl ((4aR,7aR)-7a-(5-azido-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (50 mg, 0.127 mmol), 10% Pd/C (135 mg, 0.127 mmol) in methanol (5525 μL) was stirred under hydrogen balloon at rt for 12 h. The reaction mixture was filtered and the filtrate was evaporated in vacuo to tert-butyl ((4aS,7aS)-7a-(5-amino-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (44 mg, 0.120 mmol, 94% yield) as a yellowish oil. This material was used directly for the next reaction without purification. MS (M+H)+: 368.14.

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-89a5113590e0473aac02489a99adca5b
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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