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

HRID 529561Notes

Reaction equation

HRID 529561 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6][S:5][C@H:4]2[CH2:20][CH2:21][C@H:22](C(F)(F)F)[CH2:23][N:3]12.NC([C:35]([F:38])([F:37])[F:36])CCCCO.N[C@H]1CCS[C@H]2CC[C@H](C(F)(F)F)CN2C1=O>>[NH2:9][C@H:8]1[CH2:7][CH2:6][S:5][C@H:4]2[CH2:20][CH2:21][CH2:22][C@H:23]([C:35]([F:38])([F:37])[F:36])[N:3]2[C:2]1=[O:1]

Participants

4

Reactant 3

HCID 86706221(4S,8S,10aS)-4-amino-8-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-oneHCID 86706222benzyl (4S,8S,10aS)-5-oxo-8-(trifluoromethyl)octahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamateHCID 867062395-Amino-6,6,6-trifluorohexan-1-ol

Product 1

HCID 68292507(4S,7R,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Procedure

(4S,7R,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (39 mg, 0.15 mmol) was synthesized as described for the preparation of Intermediate 58 using 5-amino-6,6,6-trifluorohexan-1-ol in step A followed by the preparation of Intermediate 60. Anal. Calcd. for C10H15F3N2OS m/z 268.3. found: 269.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.29 (dd, J=4.4, 2.8 Hz, 1H), 5.13-4.99 (m, 1H), 3.95 (dd, J=10.6, 3.6 Hz, 1H), 3.07 (ddd, J=14.5, 10.0, 3.3 Hz, 1H), 2.74 (ddd, J=14.6, 6.7, 3.3 Hz, 1H), 2.48-2.29 (m, 2H), 2.24 (ddt, J=13.8, 6.9, 3.4 Hz, 1H), 2.16-2.02 (m, 2H), 1.94-1.69 (m, 5H).

Sources & evidence

ORD record
ord-e487b5aa83124b59a74c51a8504f2aec
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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