Cyclohexanemethylamine → (1R,2S)-1 {[(2S,4R)-1-[(1S)-1-(Cyclohexylmethyl-carbamoyl)-2-phenyl-ethylcarbamoyl]4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

HRID 1822445Notes

Reaction equation

HRID 1822445 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])(C)(C)C.C(OC(NC(C(C)(C)C)C(O)=O)=O)(C)(C)C.[CH:36]1([CH2:42][NH2:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:77][C:78]([C:80]1([NH:85][C:86]([CH:88]2[CH2:92][CH:91]([O:93][C:94]3[C:103]4[C:98](=[CH:99][C:100]([O:104][CH3:105])=[CH:101][CH:102]=4)[N:97]=[C:96]([C:106]4[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=4)[CH:95]=3)[CH2:90][N:89]2C(=O)NC(C(=O)NC2C3C(=CC=CC=3)CC2O)C(C)(C)C)=[O:87])[CH2:82][CH:81]1[CH:83]=[CH2:84])=[O:79])C>>[CH:36]1([CH2:42][NH:43][C:17]([C@@H:9]([NH:8][C:6]([N:89]2[CH2:90][C@H:91]([O:93][C:94]3[C:103]4[C:98](=[CH:99][C:100]([O:104][CH3:105])=[CH:101][CH:102]=4)[N:97]=[C:96]([C:106]4[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=4)[CH:95]=3)[CH2:92][C@H:88]2[C:86]([NH:85][C@:80]2([C:78]([OH:79])=[O:77])[CH2:82][C@H:81]2[CH:83]=[CH2:84])=[O:87])=[O:7])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:19])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

7

Reactant 6

HCID 76688CyclohexanemethylamineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 22035886ChlorocarbamateHCID 68488177[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propyl]-carbamic acid tert.butyl esterHCID 684916281-{[1-[1-(2-Hydroxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68488115(1R,2S)-1 {[(2S,4R)-1-[(1S)-1-(Cyclohexylmethyl-carbamoyl)-2-phenyl-ethylcarbamoyl]4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid

Procedure

N-(tert-butoxycarbonyl)-L-phenylalanine was attached to the resin as described for the preparation of compound 16 followed by reaction with cyclohexanemethylamine as described for the preparation of 17 and removal of the Boc group as described for 18. The afforded compound was then reacted with the chlorocarbamate achieved from 12 as described for the preparation of 13 which gave the title compound. Purity by HPLC>95%. M+H+760.4.

Sources & evidence

ORD record
ord-e05eed28e35247ca8f3ef57c59c64229
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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