tert-butyl (3S)-3-amino-3-(1,3-dioxaindan-5-yl)propanoate → (s)-3-((s)-2-((s)-4-Phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(3,4-methylenedioxyphenyl)propionic acid

HRID 2230226Notes

Reaction equation

HRID 2230226 reaction equation
[C:1]1([C@@:7]2([CH3:29])[C:11](=[O:12])[N:10]([C@@H:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([O-])=[O:15])[C:9](=[O:21])[N:8]2[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:30][C@H:31]([C:40]1[CH:45]=[CH:44][C:43]2[O:46][CH2:47][O:48][C:42]=2[CH:41]=1)[CH2:32][C:33]([O:35]C(C)(C)C)=[O:34]>>[C:1]1([C@@:7]2([CH3:29])[C:11](=[O:12])[N:10]([C@@H:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([NH:30][C@H:31]([C:40]3[CH:45]=[CH:44][C:43]4[O:46][CH2:47][O:48][C:42]=4[CH:41]=3)[CH2:32][C:33]([OH:35])=[O:34])=[O:15])[C:9](=[O:21])[N:8]2[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 57048399tert-butyl (3S)-3-amino-3-(1,3-dioxaindan-5-yl)propanoateHCID 131723411(s)-2-((s)-4-Phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetate

Product 1

HCID 59902377(s)-3-((s)-2-((s)-4-Phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(3,4-methylenedioxyphenyl)propionic acid

Procedure

The compound was prepared analogously to Example 1 by reaction of 169.5 with tert-butyl (S)-3-amino-3-(3,4-methylenedioxyphenyl)propionate (prepared analogously to S. G. Davis et al., Tetrahedron Asymmetry 1991, 2, 183), cleavage of the tert-butyl ester with trifluoroacetic acid as described in Example 1, and subsequent purification of the crude product by means of preparative HPLC (RP18: eluent: acetonitrile/water=50/120). ES(+)-MS: 586.4 (M+H)+

Workup

  1. customprepared analogously to S
  2. customDavis et al., Tetrahedron Asymmetry 1991, 2, 183), cleavage of the tert-butyl ester with trifluoroacetic acid as described in Example 1, and subsequent purification of the crude product by means of preparative HPLC (RP18: eluent: acetonitrile/water=50/120)

Sources & evidence

ORD record
ord-5675da46bf044ede8320939de439865d
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

Loading…