3-Nitrophenol → HCID 66618596, compound

HRID 1009976Notes

Reaction equation

HRID 1009976 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([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]O)[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]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:20][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 111373-NitrophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57699897N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine cyclopentyl ester

Product 1

HCID 66618596HCID 66618596, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 3-nitrophenol (1.2 g, 8.4 mmol) in anhydrous DCM (60 ml) at 0° C. was added (S)-2-tert-butoxycarbonylamino-4-hydroxy-butyric acid cyclopentyl ester (2 g, 7 mmol) (see Scheme 9) in DCM (10 ml), triphenyl phosphine (7.5 g, 28.7 mmol) followed by slow addition of DIAD (5.8 g, 28.7 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. (EtOAc:heptane, 1:9), (1.6 g, 56%). LCMS purity 95%, 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-bbae6b2445d543179971120f0a3a8389
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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