(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid → HCID 178495680, compound

HRID 1751685Notes

Reaction equation

HRID 1751685 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:10]([N:12]1[CH2:16][C@@H:15]([CH2:17][O:18][CH3:19])[CH2:14][C@H:13]1[C:20]1[NH:24][C:23]2[C:25]3[C:30]([CH:31]=[CH:32][C:22]=2[N:21]=1)=[CH:29][C:28]([C:33]1[CH:34]=[C:35]2[C:60](=[CH:61][CH:62]=1)[C:39]1[NH:40][C:41]([C@@H:43]4[CH2:47][C@H:46](C)[CH2:45][N:44]4[C:49](=[O:59])[C@@H:50]([NH:54][C:55](=[O:58])[O:56][CH3:57])[CH:51]([CH3:53])[CH3:52])=[N:42][C:38]=1C=C2)=[CH:27][CH:26]=3)=[O:11])=[O:7])(C)(C)C.[F:69][CH:70]([F:127])[O:71]C1C=C(C2NC([C@@H]3CCCN3C(=O)[C@@H](NC(OC)=O)C(C)C)=NC=2)C=CC=1C1C=C2C(=CC=1)C1NC([C@@H]3C[C@H](COC)CN3C(OC(C)(C)C)=O)=NC=1C=C2.C(OC(N[C@H](C1C=CC=CC=1)C(O)=O)=O)(C)(C)C.COC(N[C@H](C1C=CC=CC=1)C(O)=O)=O>>[CH3:1][O:5][C:6]([NH:8][C@H:9]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:10]([N:12]1[CH2:16][C@@H:15]([CH2:17][O:18][CH3:19])[CH2:14][C@H:13]1[C:20]1[NH:24][C:23]2[C:25]3[C:30]([CH:31]=[CH:32][C:22]=2[N:21]=1)=[CH:29][C:28]([C:33]1[CH:62]=[CH:61][C:60]([C:39]2[NH:40][C:41]([C@@H:43]4[CH2:47][CH2:46][CH2:45][N:44]4[C:49](=[O:59])[C@H:50]([NH:54][C:55](=[O:58])[O:56][CH3:57])[CH:51]([CH3:52])[CH3:53])=[N:42][CH:38]=2)=[CH:35][C:34]=1[O:71][CH:70]([F:127])[F:69])=[CH:27][CH:26]=3)=[O:11])=[O:7]

Participants

5

Reactant 4

HCID 2755953(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acidHCID 10910775(alphaR)-alpha-((Methoxycarbonyl)amino)benzeneacetic acidHCID 178495675HCID 178495675, compoundHCID 178495681HCID 178495681, compound

Product 1

HCID 178495680HCID 178495680, compound

Procedure

Methyl (R)-1-((S)-2-(5-(4-(2-((2S,4S)-1-((R)-2-methoxycarbonylamino-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl)-3-(difluoromethoxy)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate was prepared according to the method employed in the synthesis of methyl (S)-1-((2S,4S)-2-(2′-((2S,4S)-1-((R)-2-tert-butoxycarbonylamino-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate, substituting (2S,4S)-tert-butyl 2-(2′-((2S,4S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-methylpyrrolidin-2-yl)-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate with (2S,4S)-tert-butyl 2-(7-(2-(difluoromethoxy)-4-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)-1H-naphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate and (R)-2-(tert-butoxycarbonylamino)-2-phenylacetic acid with (R)-2-(methoxycarbonylamino)-2-phenylacetic acid. MS (ESI) m/z 907 [M+H]+.

Sources & evidence

ORD record
ord-88fddfabe9414048af549f2afd5dbea3
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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