Triphenylphosphine → HCID 118101215, compound

HRID 708901Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[F:15][C:16]1[C:17]([OH:35])=[C:18]([CH:29]=[C:30]([N+:32]([O-])=O)[CH:31]=1)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].[CH3:36][O:37][CH2:38][CH2:39][CH2:40]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1.CO.[Zn]>[NH2:32][C:30]1[CH:31]=[C:16]([F:15])[C:17]([O:35][CH2:40][CH2:39][CH2:38][O:37][CH3:36])=[C:18]([CH:29]=1)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

DIAD was added to a solution of 17D (751 mg, 2.5 mmol), 3-methoxypropan-1-ol (496 mg, 5.50 mmol), triphenylphosphine (1443 mg, 5.50 mmol) in THF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, and rt for 16 h. The mixture was concentrated and purified by flash chromatography (0-50% EtOAc in hexanes) to give a light yellow solid. The obtained solid was dissolved in MeOH (20 mL) and THF (5 mL). Zinc (1635 mg, 25.00 mmol) and ammonium chloride (2.64 mL, 75 mmol) was added. The reaction mixture was stirred rt for 2 h. After aqueous work up and extraction, the crude product was purified by flash chromatography to give 28A (900 mg, 2.63 mmol, 105% yield). MS (ESI) m/z: 343.1 (M+H)+.

Workup

waitrt for 16 h
concentrationThe mixture was concentrated
custompurified by flash chromatography (0-50% EtOAc in hexanes)
customto give a light yellow solid
stirringThe reaction mixture was stirred rt for 2 h
extractionAfter aqueous work up and extraction
customthe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-6802eea70e544a73ad1ab0b2cf738137
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174974B2

Reaction notes

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