Triphenylphosphine → HCID 59852612, compound

HRID 2373827Notes

Reaction equation

HRID 2373827 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:22][C:23]([C:25]1[C:34]([OH:35])=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](C2C=CC3C(=CC=CC=3)C=2)=[CH:8][CH:7]=1.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][OH:46])=[CH:40][CH:39]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:36])[C@@H:4]([NH:22][C:23]([C:25]1[C:34]([OH:35])=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:46][CH2:45][CH2:44][C:41]2[CH:42]=[CH:43][C:38]([Cl:37])=[CH:39][CH:40]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74647p-Chlorophenethylic alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 59852579HCID 59852579, compound

Product 1

HCID 59852612HCID 59852612, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.05 g (0.1 mmol) of resin-bound 2-(S)-(3-Hydroxy-naphthalene-2-carbonyl)-amino-3-(4-hydroxy-phenyl)-propionic acid methyl ester obtained in Example 105 was reacted with 2-(4-chloro-phenyl)-ethanol (156 mg, 1.0 mmol), DIAD (1.0 mmol), Ph3P (1.0 mmol) in THF at rt overnight. The resulting resin was hydrolyzed according to general procedure C. The resin was then washed and cleaved as described in Example 28 to give the title compound (20 mg). LC/MS (m/z) 490 (M+1)+.

Workup

  1. washThe resin was then washed

Sources & evidence

ORD record
ord-b80744de44e04e1e83fc27ffb6b9afd5
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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