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

HRID 529560Notes

Reaction equation

HRID 529560 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 68292539(4S,8R,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-ylcarbamateHCID 867062395-Amino-6,6,6-trifluorohexan-1-ol

Product 1

HCID 86706238(4S,7S,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one

Procedure

(4S,7S,10aS)-4-Amino-7-(trifluoromethyl)hexahydro-2H-pyrido[2,1-b][1,3]thiazepin-5(7H)-one (53 mg, 0.20 mmol) was synthesized as described for the preparation of Intermediate 59 using 5-amino-6,6,6-trifluorohexan-1-ol in step A followed by the preparation of Intermediate 61. Anal. Calcd. for C10H15F3N2OS m/z 268.3. found: 269.0 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 5.42-5.27 (m, 1H), 5.21 (t, J=7.0 Hz, 1H), 3.99 (dd, J=10.3, 2.7 Hz, 1H), 3.15 (ddd, J=13.9, 10.9, 2.6 Hz, 1H), 2.81 (ddd, J=14.4, 6.3, 2.9 Hz, 1H), 2.23 (ddt, J=14.2, 6.0, 2.9 Hz, 1H), 2.19-2.07 (m, 1H), 2.06-1.79 (m, 7H), 1.54-1.39 (m, 1H).

Sources & evidence

ORD record
ord-43ee00327f8647c8af19468193ebca8c
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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