3-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid → 3-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]-butanamide

HRID 1591452Notes

Reaction equation

HRID 1591452 reaction equation
[NH2:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[S:3]1.[C:13]([O:17][C:18]([NH:20][C:21]([CH3:27])([CH3:26])[CH2:22][C:23](O)=[O:24])=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([NH:20][C:21]([CH3:27])([CH3:26])[CH2:22][C:23]([NH:1][CH:2]1[C:7](=[O:8])[NH:6][C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[S:3]1)=[O:24])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acidHCID 107974522-Amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine

Product 1

HCID 190257203-t-Butoxycarbonylamino-3-methyl-N-[3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]-butanamide

Procedure

Prepared from 2-amino-3,4-dihydro-3-oxo-2H-1,4-benzothiazine (Step A) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (Example 31, Step E) by the procedure described in Example 1, Step F. 1H NMR (200 MHz, CD3OD): 1.26 (s,6H), 1.36 (s,9H), 2.47 (d,13 Hz,1H), 2.57 (d,13 Hz,1H), 5.52 (br s,1H), 6.31 (br s,1H), 7.00 (m,2H), 7.22 (m,2H). FAB-MS: calculated for C18H25N3O4S 379; found 380 (M+H,26%).

Sources & evidence

ORD record
ord-73ccafd2fc184017bf22bded6c913327
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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