Boc-L-Valine → HCID 57893049, compound

HRID 1822453Notes

Reaction equation

HRID 1822453 reaction equation
C(OC(N[C@@H](C(C)C)C(O)=O)=O)(C)(C)C.C(OC(NC(C(C)(C)C)C(O)=O)=O)(C)(C)C.[NH2:32][C@@H:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][C@@H:34]1[OH:42].C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:76][C:77]([C:79]1([NH:84][C:85]([CH:87]2[CH2:91][CH:90]([O:92][C:93]3[C:102]4[C:97](=[CH:98][C:99]([O:103][CH3:104])=[CH:100][CH:101]=4)[N:96]=[C:95]([C:105]4[CH:110]=[CH:109][CH:108]=[CH:107][CH:106]=4)[CH:94]=3)[CH2:89][N:88]2[C:111](=[O:131])[NH:112][CH:113]([C:118](=[O:130])NC2C3C(=CC=CC=3)CC2O)[C:114](C)([CH3:116])[CH3:115])=[O:86])[CH2:81][CH:80]1[CH:82]=[CH2:83])=[O:78])C>>[OH:42][C@H:34]1[CH2:35][C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:33]1[NH:32][C:118]([C@@H:113]([NH:112][C:111]([N:88]1[CH2:89][C@H:90]([O:92][C:93]2[C:102]3[C:97](=[CH:98][C:99]([O:103][CH3:104])=[CH:100][CH:101]=3)[N:96]=[C:95]([C:105]3[CH:106]=[CH:107][CH:108]=[CH:109][CH:110]=3)[CH:94]=2)[CH2:91][C@H:87]1[C:85]([NH:84][C@:79]1([C:77]([OH:78])=[O:76])[CH2:81][C@H:80]1[CH:82]=[CH2:83])=[O:86])=[O:131])[CH:114]([CH3:116])[CH3:115])=[O:130]

Participants

7

Reactant 6

HCID 83693Boc-L-ValineHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 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 57893049HCID 57893049, compoundYield 24%

Procedure

(2S)-tert-butoxycarbonylamino-3-methylbutyric acid was attached to the resin as described for the preparation of compound 16 followed by reaction with (1R,2S)-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 (11 mg, 24% yield), Purity by HPLC >75% M+H+748.

Workup

  1. customafter purification by HPLC

Sources & evidence

ORD record
ord-ac5ad8c69f2e41d5a482317e4408ea96
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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