(S)-tert-Butyl 2-amino-3-(tert-butoxy)propanoate → (s)-3-Tert-butoxy-2-{3-[5-(5,6-difluoro-1h-indol-2-yl)-2-methoxy-phenyl]-thioureido}-propionic acid tert-butyl ester

HRID 25520Notes

Reaction equation

HRID 25520 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([N:18]=[C:19]=[S:20])[CH:17]=1)=[CH:5]2.[C:23]([O:27][C:28](=[O:37])[C@H:29]([CH2:31][O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[NH2:30])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28](=[O:37])[C@@H:29]([NH:30][C:19]([NH:18][C:16]1[CH:17]=[C:12]([C:6]2[NH:7][C:8]3[C:4]([CH:5]=2)=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=3)[CH:13]=[CH:14][C:15]=1[O:21][CH3:22])=[S:20])[CH2:31][O:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:26])([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 6993439(S)-tert-Butyl 2-amino-3-(tert-butoxy)propanoateHCID 225684385-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl isothiocyanate2×

Product 1

HCID 10302130(s)-3-Tert-butoxy-2-{3-[5-(5,6-difluoro-1h-indol-2-yl)-2-methoxy-phenyl]-thioureido}-propionic acid tert-butyl ester

Procedure

The product from Example 35, Step A, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl isothiocyanate (0.316 g, 1.0 mmol) was reacted with serine tert-butylether tert-butylester (0.226 g, 1.0 mmol) according to the procedure for Example 23, Step B to give the product after filtration through silica gel using hexanes/ethyl acetate, 1/1, v/v as eluant (0.377 g in 2 portions), mp 111-114° C.

Workup

  1. customto give the product
  2. filtrationafter filtration through silica gel

Sources & evidence

ORD record
ord-cfb9dcc521dc451dac39b85d1d681c67
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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