HCID 57386558, compound → HCID 131729390, compound

HRID 420316Notes

Reaction equation

HRID 420316 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[C:22](F)[C:21]([N+:25]([O-:27])=[O:26])=[C:20]([F:28])[CH:19]=2)[CH2:13][S:12](=[O:30])(=[O:29])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[F:34][C:35]([F:42])([F:41])[C@H:36]([OH:40])[CH2:37][O:38][CH3:39]>>[C:1]([C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[C:22]([O:40][C@H:36]([CH2:37][O:38][CH3:39])[C:35]([F:42])([F:41])[F:34])[C:21]([N+:25]([O-:27])=[O:26])=[C:20]([F:28])[CH:19]=2)[CH2:13][S:12](=[O:29])(=[O:30])[CH2:11]1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 57386558HCID 57386558, compoundHCID 866395432-Propanol, 1,1,1-trifluoro-3-methoxy-, (2R)-

Product 1

HCID 131729390HCID 131729390, compound

Procedure

The title compound was prepared in analogous manner as described for example 24j) from (3R,4S,5S)-3-(3-tert-butyl-benzylamino)-5-(3,5-difluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol (example 24i) and (R)-1,1,1-trifluoro-3-methoxy-propan-2-ol to yield the title compound as a colorless foam: TLC (EtOAc-MeOH 19:1) Rf=0.47; HPLC RtA=2.13 min; ESIMS [M+H]+=607; 1H NMR (600 MHz, DMSO-d6): δ 7.34 (s, 1H), 7.28 (s, 1H), 7.24 (m, 2H), 7.143 (d, 1H), 7.10 (d, 1H), 5.59 (m, 1H), 5.30 (d, 1H), 3.80 (m, 2H), 3.70 (dd, 1H), 3.64 (d, 1H), 3.40 (dt, 1H), 3.29 (s, 3H), 3.21 (m, 1H), 3.12 (dd, 1H), 3.03 (m, 2H), 2.81 (m, 1H), 2.62 (dd, 1H), 2.42 (m, 1H), 2.14 (m, 1H), 1.27 (s, 9H).

Workup

  1. customThe title compound was prepared in analogous manner

Sources & evidence

ORD record
ord-d84c8334bb0f4b80b6b3153e0b9f287e
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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