Acetonitrile → HCID 18790171, compound

HRID 1107158Notes

Reaction equation

HRID 1107158 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH:12]([C:23]2([C:28]([OH:30])=O)[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CC#[N:33].C(O)(C(F)(F)F)=O.[OH2:41]>>[OH:41][NH:33][C:28]([C:23]1([CH:12]([S:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:30]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 18790061HCID 18790061, compoundHCID 22392675Trifluoroacetic acid water

Product 1

HCID 18790171HCID 18790171, compoundYield 29%

Procedure

The procedure Example 38, Step E is used. From 1-[1-(3,4-Dimethoxyphenylsulfanyl)-5-phenylpentyl]cyclopentane carboxylic acid (0.5 g, 1.2 mmol) the impure product is purified by reverse-phase HPLC (50 to 100% CH3CN in 0.1% TFA/H2O, 30 minutes) to yield 1-[1-(3,4-Dimethoxyphenylsulfanyl)-5-phenylpentyl]cyclopentane carboxylic acid hydroxyamide (0.15 g, 29%): 1H NMR (300 MHz, CDCl3) δ 9.03 (bs, 1H), 7.70 (bs, 1H), 7.29-7.24 (m, 2H), 7.20-7.13 (m, 3H), 6.99 (dd, J=8.2, 2.0 Hz, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.78 (d, J=8.5 Hz, 1H), 3.87 (s, 3H), 3.85 (s, 3H), 3.04 (d, J=11.0 Hz, 1H), 2.63-2.57 (m, 2H), 2.38-2.30 (m, 1H), 1.97-1.93 (m, 1H), 1.81-1.38 (m, 12H); MS (EI) m/e 443 (M+).

Sources & evidence

ORD record
ord-ca60b0678c444b309b0e4810c67da196
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

Loading…