HCID 57429690, compound → HCID 68555765, compound

HRID 420287Notes

Reaction equation

HRID 420287 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][C:12]=1[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:24][C:25]([CH:27]1[C:32](=[O:33])[CH:31]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30][S:29][CH2:28]1)=[O:26])[CH:22]=[CH2:23]>C1CCCCC1.CCOC(C)=O>[CH2:21]([O:24][C:25]([C@@:27]1([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:20])=[C:12]([F:19])[CH:13]=2)[C:32](=[O:33])[CH:31]([NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30][S:29][CH2:28]1)=[O:26])[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 57429690HCID 57429690, compoundHCID 666496495-tert-Butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester

Product 1

HCID 68555765HCID 68555765, compound

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

The title compound was prepared in analogous manner as described for example 1c from (4-bromomethyl-2-fluoro-phenyl)-carbamic acid benzyl ester (37 g, 109 mmol) and 5-tert-butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester (33 g, 105 mmol, example 1b) to yield a diastereomeric mixture of a yellow solid: TLC (cyclohexane-EtOAc 1:1) Rf=0.77; ESIMS [M+NH4]+=590; LCMS [M+NH4]+=590, RtI=1.60 min.

Workup

  1. customto yield
  2. additiona diastereomeric mixture of a yellow solid
  3. customLCMS [M+NH4]+=590, RtI=1.60 min.

Sources & evidence

ORD record
ord-fa531992ed0b4c95a90df51eb8e6c8ed
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

Loading…