Trifluoroacetic acid → (S)-3-((S)-2-((S)-4-Phenyl-3-((4-biphenylyl)methyl)4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(3,4-methylenedioxyphenyl)propionic acid

HRID 1883101Notes

Reaction equation

HRID 1883101 reaction equation
[C:1]1([C@@:7]2([CH3:35])[C:11](=[O:12])[N:10]([C@@H:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([OH:16])=O)[C:9](=[O:21])[N:8]2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=CC([C@@]2(C)C(=O)N([C@@H](CC(C)C)C(OC(C)(C)C)=O)C(=O)N2)=CC=1.C1(C2C=CC(CBr)=CC=2)C=CC=CC=1.C1([C@@]2(C)C(=O)N([C@@H](CC(C)C)C([O-])=O)C(=O)N2CC2C=CC=CC=2)C=CC=CC=1.[NH2:106][C@H:107]([C:116]1[CH:121]=[CH:120][C:119]2[O:122][CH2:123][O:124][C:118]=2[CH:117]=1)[CH2:108][C:109]([O:111]C(C)(C)C)=[O:110].FC(F)(F)C(O)=O>>[C:1]1([C@@:7]2([CH3:35])[C:11](=[O:12])[N:10]([C@@H:13]([CH2:17][CH:18]([CH3:19])[CH3:20])[C:14]([NH:106][C@H:107]([C:116]3[CH:121]=[CH:120][C:119]4[O:122][CH2:123][O:124][C:118]=4[CH:117]=3)[CH2:108][C:109]([OH:111])=[O:110])=[O:16])[C:9](=[O:21])[N:8]2[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:27][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 6

HCID 6422Trifluoroacetic acidHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 57048399tert-butyl (3S)-3-amino-3-(1,3-dioxaindan-5-yl)propanoateHCID 69083920(S)-2-((S)-4-phenyl-3-((4-biphenylyl)methyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetic acidHCID 86588628tert-Butyl (S)-2-((S)-4-(4-bromophenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetateHCID 131723411(s)-2-((s)-4-Phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetate

Product 1

HCID 59902397(S)-3-((S)-2-((S)-4-Phenyl-3-((4-biphenylyl)methyl)4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-(3,4-methylenedioxyphenyl)propionic acid

Procedure

(by reaction of (S)-2-((S)-4-phenyl-3-((4-biphenylyl)methyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetic acid (obtainable by reaction of 169.2 with 4-phenylbenzyl bromide analogously to the synthesis of 169.3 and subsequent reactions analogously to the preparation of 169.5) with tert-butyl (S)-3-amino-3-(3,4-methylenedioxyphenyl)propionate and subsequent cleavage of the tert-butyl ester with trifluoroacetic acid)

Workup

  1. customanalogously to the synthesis of 169.3 and subsequent reactions

Sources & evidence

ORD record
ord-9f33a28cdc4f4657bbcbc63bb466e082
Source dataset
uspto-grants-2004_07
Patent number
US06759424B2

Reaction notes

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