Boc-L-Valine → HCID 57893029, compound

HRID 1822450Notes

Reaction equation

HRID 1822450 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][CH2:34]1.C(OC(=O)NC(C(=O)NC1C2C(=CC=CC=2)CC1O)C(C)(C)C)(C)(C)C.ClNC(=O)[O-].C([O:75][C:76]([C:78]1([NH:83][C:84]([CH:86]2[CH2:90][CH:89]([O:91][C:92]3[C:101]4[C:96](=[CH:97][C:98]([O:102][CH3:103])=[CH:99][CH:100]=4)[N:95]=[C:94]([C:104]4[CH:109]=[CH:108][CH:107]=[CH:106][CH:105]=4)[CH:93]=3)[CH2:88][N:87]2[C:110](=[O:130])[NH:111][CH:112]([C:117](=[O:129])NC2C3C(=CC=CC=3)CC2O)[C:113](C)([CH3:115])[CH3:114])=[O:85])[CH2:80][CH:79]1[CH:81]=[CH2:82])=[O:77])C>>[C@@H:33]1([NH:32][C:117]([C@@H:112]([NH:111][C:110]([N:87]2[CH2:88][C@H:89]([O:91][C:92]3[C:101]4[C:96](=[CH:97][C:98]([O:102][CH3:103])=[CH:99][CH:100]=4)[N:95]=[C:94]([C:104]4[CH:105]=[CH:106][CH:107]=[CH:108][CH:109]=4)[CH:93]=3)[CH2:90][C@H:86]2[C:84]([NH:83][C@:78]2([C:76]([OH:77])=[O:75])[CH2:80][C@H:79]2[CH:81]=[CH2:82])=[O:85])=[O:130])[CH:113]([CH3:115])[CH3:114])=[O:129])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34]1

Participants

7

Reactant 6

HCID 83693Boc-L-ValineHCID 50468592-{[(Tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 70000841-Aminoindane, (S)-HCID 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 57893029HCID 57893029, compoundYield 49%

Procedure

(2S)-tert-butoxycarbonylamino-3-methylbutyric acid was attached to the resin as described for the preparation of compound 16 followed by reaction with (1S)-1-aminoindane 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 (22 mg, 49% yield), Purity by HPLC>90% M+H+732.2.

Workup

  1. customafter purification by HPLC

Sources & evidence

ORD record
ord-a033a298909a4a8abf65d6f99a889b31
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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