Lawesson's reagent → HCID 10552280, compound

HRID 322883Notes

Reaction equation

[C:1]([C:4]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)=[CH:22][C:5]=1[O:6][CH:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)[NH2:2].COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:42]2)=CC=1>O1CCCC1>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:7]([O:6][C:5]1[CH:22]=[C:23]([O:26][CH2:27][C:28]2[CH:32]=[CH:31][S:30][CH:29]=2)[CH:24]=[CH:25][C:4]=1[C:1](=[S:42])[NH2:2])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 25 °C

Procedure

A stirred solution of ethyl (RS)-4-[2-carbamoyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (2.44 g) in tetrahydrofuran (49 mL) is treated with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide (1.08 g) and maintained at 25° C. for 24 hours. The solution is then evaporated and the residual oil is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (2:1 v/v), followed by trituration with diethyl ether, to give ethyl (RS)-4-(2-methylphenyl)-4-[5-(3-thienylmethoxy)-2-thiocarbamoylphenoxy]butanoate (1.79 g) in the form of a yellow solid, m.p. 134-135° C. [NMR(CDCl3):- 1.2(3H,t),2.2-2.6(4H,m), 2.4(3H,s),4.1(2H,q), 4.9(2H,q),5.6(1H,m),6.2-7.8(9H,m),8.7(1H,d)].

Workup

customThe solution is then evaporated
washeluting with a mixture of pentane and ethyl acetate (2:1 v/v)

Sources & evidence

ORD record: ord-87524570f37e498db86fbdf53a92c85c
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Reaction notes

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