4-Nitrophenol → HCID 14347604, compound

HRID 1651118Notes

Reaction equation

[C:1]1([C:7]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][C@@H:8]2[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([O:13][C:12](=[O:14])[CH2:11][CH2:10][C@H:8]2[CH2:9][C:7]2([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

Conditions

Temperature: 25 °C

Procedure

As in Example 111, (S)-2,2-diphenylcyclopropanepropanoic acid (6.38 g) and 4-nitrophenol (4 g) in dichloromethane (100 mL) was treated with 1,3-dicyclohexylcarbodiimide (4.95 g) and the mixture was stirred at 25° C. for 1 hour. The crude ester, isolated in the usual way, was crystallized from 2-propanol to give 4.8 g of (S)-2,2-diphenylcyclopropanepropanoic acid 4-nitrophenyl ester. The analytical sample was obtained from the same solvent, mp 76°-77° C.; [α]D25 -93.53° (c, 1.0, MeOH).

Workup

customThe crude ester, isolated in the usual way
customwas crystallized from 2-propanol

Sources & evidence

ORD record: ord-bbaaf0d9d4c24e3485f03fcba95bbe20
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04927826

Reaction notes

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