Oxalyl chloride → (+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanohydroxamic acid

HRID 381387Notes

Reaction equation

HRID 381387 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][C:18](O)=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:39][NH2:40]>CN(C)C=O.ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][C:18]([NH:40][OH:39])=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 18363145(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid

Product 1

HCID 18363141(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanohydroxamic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of (±)-3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid (0.40 g, Example 4) in a mixture of dimethylformamide (0.07 ml) and dichloromethane (20 ml) was treated dropwise with a solution of oxalyl chloride in dichloromethane (1.17 ml, 2.0 M). After stirring at room temperature for a further 30 minutes the mixture was treated dropwise with O-(trimethylsilyl)hydroxylamine (0.57 ml). The resulting white suspension was stirred for 10 minutes then partitioned between hydrochloric acid (50 ml, 1N) and ethyl acetate (50 ml). The aqueous layer was extracted twice with ethyl acetate (50 ml). The combined organic phases were washed with water (50 ml), then with brine (50 ml), then dried over magnesium sulphate and then evaporated to give the title compound (0.26 g) as a white foam. NMR (CDCl3): δ1.60 (m,8H), 1.86 (m,6H), 2.35 (br d,2H), 2.60 (br t,2H), 3.30 (m,1H), 3.80 (s,3H), 3.73 (m,1H), 6.76 (d,1H), 6.95 (d,2H), 7.10-7.30 (m,5H). Mass spectrum (FAB): m/z 444 (M+H)+.

Workup

  1. stirringThe resulting white suspension was stirred for 10 minutes
  2. customthen partitioned between hydrochloric acid (50 ml, 1N) and ethyl acetate (50 ml)
  3. extractionThe aqueous layer was extracted twice with ethyl acetate (50 ml)
  4. washThe combined organic phases were washed with water (50 ml)
  5. dry with materialwith brine (50 ml), then dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-7e91a487fd2445d2b2ee5edeacb13383
Source dataset
uspto-grants-2001_10
Patent number
US06306873B1

Reaction notes

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