Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate → 2-Tert-butoxycarbonylamino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester

HRID 1245390Notes

Reaction equation

HRID 1245390 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:6]=[CH2:7].[CH3:17][C:18]1[CH:27]=[C:26]([CH2:28][O:29][C:30]2[CH:38]=[CH:37][C:33]([CH:34]=[N:35][OH:36])=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>>[CH3:1][O:2][C:3](=[O:16])[CH:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:6]1[O:36][N:35]=[C:34]([C:33]2[CH:32]=[CH:31][C:30]([O:29][CH2:28][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([CH3:17])[CH:27]=3)=[CH:38][CH:37]=2)[CH2:7]1

Participants

3

Reactant 2

HCID 10857232Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoateHCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime

Product 1

HCID 696398152-Tert-butoxycarbonylamino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl esterYield 65%

Procedure

Following a procedure analogous to that used in Example step 1c, but using the product from step 8b and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime from step 1b, the crude product was prepared and purified by FCC on silica gel eluting ethyl acetate:hexanes (gradient) to give 2-tert-butoxycarbonylamino-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (1.15 g, 65%) as an oil. MS found: (M+H)+=520.

Workup

  1. customthe crude product was prepared
  2. custompurified by FCC on silica gel
  3. washeluting ethyl acetate

Sources & evidence

ORD record
ord-2f0f5701113249c7a4166404ca2012c4
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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