Isobutanol → HCID 131733460, compound

HRID 2278369Notes

Reaction equation

HRID 2278369 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([C:24]1[S:28][C:27]([CH2:29][NH:30][C:31](=[O:51])[C@H:32]([CH:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[NH:33][C:34]([O:36][CH3:37])=[O:35])=[CH:26][CH:25]=1)[NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:71](O)[CH:72]([CH3:74])[CH3:73].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@H:10]([C:24]1[S:28][C:27]([CH2:29][NH:30][C:31](=[O:51])[C@H:32]([CH:38]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[NH:33][C:34]([O:36][CH3:37])=[O:35])=[CH:26][CH:25]=1)[N:11]([CH2:71][CH:72]([CH3:74])[CH3:73])[S:12]([C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)(=[O:13])=[O:14])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 6560IsobutanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 131733459HCID 131733459, compound

Product 1

HCID 131733460HCID 131733460, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-({5-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-{[(4-nitrophenyl)sulfonyl]amino}ethyl]thiophen-2-yl}methyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenyl alaninamide (60 mg, 0.080 mmol), Ph3P (105 mg, 0.398 mmol), isobutanol (0.037 mL, 0.398 mmol) and DIAD (0.077 mL, 0.398 mmol) in THF (0.4 mL) stirred at 40° C. under N2 atmosphere, for 18 hours. Ethyl acetate and water were added and the phases were separated. The organic phase was washed with brine, dried, and concentrated under reduce pressure. The concentrate was purified on silica gel using 5%-65% ethyl acetate in hexane to afford the title compound with impurities. MS: m/z=810.3 ((MH+)).

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe concentrate was purified on silica gel using 5%-65% ethyl acetate in hexane

Sources & evidence

ORD record
ord-19cd932dc5c240429393500e7effe68d
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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