2-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid → HCID 57892951, compound

HRID 1822456Notes

Reaction equation

HRID 1822456 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10]([OH:12])=O)=[O:7])(C)(C)C.C(OC(NC(C(C)(C)C)C(O)=O)=O)(C)(C)C.[NH2:36][C@H:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][C@H:38]1[OH:46].C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:80][C:81]([C:83]1([NH:88][C:89]([CH:91]2[CH2:95][CH:94]([O:96][C:97]3[C:106]4[C:101](=[CH:102][C:103]([O:107][CH3:108])=[CH:104][CH:105]=4)[N:100]=[C:99]([C:109]4[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=4)[CH:98]=3)[CH2:93][N:92]2C(=O)NC(C(=O)NC2C3C(=CC=CC=3)CC2O)C(C)(C)C)=[O:90])[CH2:85][CH:84]1[CH:86]=[CH2:87])=[O:82])C>>[CH:14]1([CH2:13][C@H:9]([NH:8][C:6]([N:92]2[CH2:93][C@H:94]([O:96][C:97]3[C:106]4[C:101](=[CH:102][C:103]([O:107][CH3:108])=[CH:104][CH:105]=4)[N:100]=[C:99]([C:109]4[CH:114]=[CH:113][CH:112]=[CH:111][CH:110]=4)[CH:98]=3)[CH2:95][C@H:91]2[C:89]([NH:88][C@:83]2([C:81]([OH:82])=[O:80])[CH2:85][C@H:84]2[CH:86]=[CH2:87])=[O:90])=[O:7])[C:10](=[O:12])[NH:36][C@H:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39][C@H:38]2[OH:46])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 6

HCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic 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 57892951HCID 57892951, compoundYield 25%

Procedure

(2S)-tert-Butoxycarbonylamino-3-cyclohexylpropanoic acid was attached to the resin as described for the preparation of compound 16 followed by reaction with (1S,2R)-1-amino-2-indanol 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, after purification by HPLC, gave the title compound (12.3 mg, 25% yield), Purity by HPLC >95% M+H+802.3.

Workup

  1. customafter purification by HPLC

Sources & evidence

ORD record
ord-3e3dd33c724e4e26ad1af15106b54e46
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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