(4R)-4-hydroxy-N,N-dimethyl-L-prolinamide trifluoroacetate → (4R)-1-{3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxyphenyl]-5-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl}-4-hydroxy-N,N-dimethy l-L-prolinamide

HRID 1662773Notes

Reaction equation

HRID 1662773 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2(O)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[NH:18][C:17]2=[O:26])=[C:12]([O:28][CH3:29])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[OH:37][C@H:38]1[CH2:42][NH:41][C@H:40]([C:43]([N:45]([CH3:47])[CH3:46])=[O:44])[CH2:39]1>>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([N:41]3[CH2:42][C@H:38]([OH:37])[CH2:39][C@H:40]3[C:43]([N:45]([CH3:47])[CH3:46])=[O:44])[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:25])[CH:23]=3)[NH:18][C:17]2=[O:26])=[C:12]([O:28][CH3:29])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 67429482(4R)-4-hydroxy-N,N-dimethyl-L-prolinamide trifluoroacetateHCID 67429824HCID 67429824, compound

Product 1

HCID 67428574(4R)-1-{3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxyphenyl]-5-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl}-4-hydroxy-N,N-dimethy l-L-prolinamide

Procedure

With 1.64 g of the compound obtained in Step 237-3 and (4R)-4-hydroxy-N,N-dimethyl-L-prolinamide trifluoroacetate (5.67 mmol) as starting materials, respectively 901 mg (Isomer A: colorless solid) and 288 mg (Isomer B: colorless amorphous) of two species of diastereoisomers of the title compound were obtained by a similar method to Step 28-2.

Sources & evidence

ORD record
ord-c2f48a3c9bd8487e9a7740c088337f5f
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

Loading…