Water → HCID 131733457, compound

HRID 2278367Notes

Reaction equation

HRID 2278367 reaction equation
C(OC(=O)[NH:6][C@@H:7]([C:17]1[S:18][C:19]([CH2:22][NH:23][C:24](=[O:44])[C@H:25]([CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:21]=1)[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])C=C.C1([SiH3])C=CC=CC=1.C(OCC)(=O)C.O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:6][C@@H:7]([C:17]1[S:18][C:19]([CH2:22][NH:23][C:24](=[O:44])[C@H:25]([CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:21]=1)[CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12752PhenylsilaneHCID 131733458HCID 131733458, compound

Product 1

HCID 131733457HCID 131733457, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of prop-2-en-1-yl{(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-[5-({[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}methyl)thiophen-2-yl]ethyl}carbamate (1.2 g, 1.841 mmol) in dichloromethane (18.4 mL) was treated with phenylsilane (6.3 mL, 5.52 mmol) and Pd(PPh3)4 (106 mg, 0.092 mmol) for 1 hour at room temperature. Ethyl acetate and water were added and the phases were separated. The organic phase was washed with brine, dried, and then concentrated under reduced pressure. The concentrate was purified on silica gel using 5%-65% ethyl acetate in hexane to afford the title compound. 1H NMR (CD3OD) δ 7.40-7.15 (11H, 6.79 (1H), 6.40 (1H), 4.98 (1H), 4.38 (1H), 4.21 (2H), 3.82 (1H), 3.70 (1H), 3.52 (3H), 0.91 (9H), 0.10 (6H).

Workup

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

Sources & evidence

ORD record
ord-936a7ff545c842e4a35e5aa6da2ba90d
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

Loading…