(4S,8S,10aS)-4-amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one → (4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

HRID 529532Notes

Reaction equation

HRID 529532 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][S:6][C@H:5]2[CH2:9][CH2:10][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:12][N:4]2[C:3]1=[O:17].O=C1[C@@H](NC(=O)OCC2C=CC=CC=2)CCS[C@H]2CC[C@@H](C(F)(F)F)CN12>>[NH2:1][C@H:2]1[CH2:8][CH2:7][S:6][C@H:5]2[CH2:9][CH2:10][C@@H:11]([C:13]([F:15])([F:14])[F:16])[CH2:12][N:4]2[C:3]1=[O:17]

Participants

3

Reactant 2

HCID 86706221(4S,8S,10aS)-4-amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-oneHCID 86706223benzyl (4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Product 1

HCID 68292539(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Procedure

(4S,8R,10aS)-4-Amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (50 mg, 0.19 mmol) was synthesized as described for the preparation of Intermediate 60 using benzyl (4S,8R,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate. Anal. Calcd. for C10H15F3N2OS m/z 268.2. found: 269.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.30 (dd, J=5.3, 3.8 Hz, 1H), 4.60 (dd, J=13.4, 4.3 Hz, 1H), 4.06 (dd, J=10.0, 4.2 Hz, 1H), 3.04 (ddd, J=14.3, 9.9, 3.0 Hz, 1H), 2.91 (t, J=12.8 Hz, 1H), 2.66 (ddd, J=14.6, 7.2, 3.1 Hz, 1H), 2.39-2.16 (m, 2H), 2.05 (dddd, J=14.5, 9.7, 7.8, 4.1 Hz, 2H), 1.94-1.85 (m, 1H), 1.80-1.64 (m, 4H).

Sources & evidence

ORD record
ord-dfbcf127ac2b43088b43c3a54453fa6f
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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