(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acid → HCID 86707731, compound

HRID 1190837Notes

Reaction equation

HRID 1190837 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([C:30]2[CH:43]=[CH:42][C:33]3[N:34]=[C:35]([CH2:37][C:38]([NH:40][NH2:41])=O)[S:36][C:32]=3[CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:19]([O:18][C:16]([NH:15][C@@H:10]([CH2:11][C:12]1[O:14][C:38]([CH2:37][C:35]2[S:36][C:32]3[CH:31]=[C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:43]=[CH:42][C:33]=3[N:34]=2)=[N:40][N:41]=1)[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:23])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 7017887(3S)-4-(benzyloxy)-3-(((tert-butoxy)carbonyl)amino)-4-oxobutanoic acidHCID 58470188HCID 58470188, compound

Product 1

HCID 86707731HCID 86707731, compoundYield 42%

Procedure

Compound 45a was prepared from (S)-4-(benzyloxy)-3-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid and 2-(6-phenylbenzo[d]thiazol-2-yl)acetohydrazide (described in WO 2011/074560) in 42% yield as a yellow solid using the general procedure given for Compound 1b. LCMS=1.13 min using analytical method (M), 571.2 (M+H). 1H NMR (400 MHz, CDCl3) δ 8.19-7.95 (m, 2H), 7.79-7.55 (m, 3H), 7.47 (t, J=7.7 Hz, 2H), 7.42-7.27 (m, 6H), 5.56 (d, J=7.0 Hz, 1H), 5.14 (s, 2H), 4.79 (br. s., 1H), 4.65 (s, 2H), 3.52-3.23 (m, 2H), 1.49-1.32 (m, 9H).

Workup

  1. customLCMS=1.13 min

Sources & evidence

ORD record
ord-cbedc83602744016be465560c0cde82c
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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