2-Nitrophenol → HCID 57831099, compound

HRID 1009977Notes

Reaction equation

HRID 1009977 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)([O-:3])=[O:2].[CH:11]1([O:16][C:17](=[O:30])[C@@H:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:20][OH:21])[CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH:11]1([O:16][C:17](=[O:30])[C@@H:18]([NH:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:19][CH2:20][O:21][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 69472-NitrophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57699897N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine cyclopentyl ester

Product 1

HCID 57831099HCID 57831099, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 4 nitrophenol (0.32 g, 2.3 mmol) in anhydrous DCM (100 ml) at 0° C. was added (S)-2-tert-butoxycarbonylamino-4-hydroxy-butyric acid cyclopentyl ester (1 g, 3.5 mmol) (Scheme 9) in DCM (100 ml), triphenyl phosphine (2.5 g, 9.5 mmol) followed by slow addition of DIAD (1.9 ml, 9.6 mmol). The reaction was allowed to warm to room temperature and stirred for 16 h. The solvent was removed and the crude material purified by column chromatography to furnish the desired product. (EtOAc:heptane, 1:9), (0.45 g, 48%). LCMS purity 97%, m/z 309 [M++H-boc]+.

Workup

  1. customThe solvent was removed
  2. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-e5c185c9434d4a56908aca968888c055
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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