Dimethyl Sulfoxide → HCID 14835090, compound

HRID 728511Notes

Reaction equation

FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[Cl:18][CH2:19][CH2:20][CH2:21][S:22]([NH:25][CH2:26][CH:27]([CH2:46][CH:47]([OH:49])[CH3:48])[CH2:28][S:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=[O:24])=[O:23].ClCCCS(NCC(CC(=O)C)COC(=O)NCCCCCCCCCCCCCCCCCC)(=O)=O>ClCCl.C(N(CC)CC)C>[Cl:18][CH2:19][CH2:20][CH2:21][S:22]([NH:25][CH2:26][CH:27]([CH2:46][C:47](=[O:49])[CH3:48])[CH2:28][S:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=[O:23])=[O:24]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled solution of 0.19 ml (1.33 mM) of trifluoroacetic anhydride in 20 ml of dichloromethane at -78° C. is added 0.19 ml (2.66 mM) of dimethylsulfoxide and the mixture is stirred at -78° C. for 5 minutes. To the reaction mixture is added a solution of 428 mg (0.83 mM) of 1-(3-chloropropylsulfonylamino)-2-(2-hydroxypropan-1-yl)-3-n-hexadecylthiopropane m15 in 2 ml of dichloromethane with stirring and the mixture is stirred at -70° C. for an additional 15 minutes. 3.50 ml (24.9 mM) of triethylamine is added and the mixture is allowed to react by the same procedure as described in (132) and 213 mg (41.6% yield) of the titled compound IIIm2 is obtained.

Workup

stirringwith stirring
stirringthe mixture is stirred at -70° C. for an additional 15 minutes
customto react by the same procedure

Sources & evidence

ORD record: ord-0f66cb14a3d64e0e96fa2fc5dbb7a8f5
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047540

Reaction notes

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