Dimethyl Sulfoxide → HCID 59997373, compound

HRID 1815577Notes

Reaction equation

HRID 1815577 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([NH:43][C:44]([O:46][C@@H:47]3[C@H:54]4[C@H:50]([O:51][CH2:52][CH2:53]4)[O:49][CH2:48]3)=[O:45])[C@H:23]([OH:42])[CH2:24][N:25]([S:30]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)(=[O:32])=[O:31])[CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[S:55]1[CH2:59][CH2:58][NH:57][CH2:56]1.CS(C)=O>O>[O:37]1[C:36]2[CH:40]=[CH:41][C:33]([S:30]([N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][C@@H:23]([OH:42])[C@@H:22]([NH:43][C:44](=[O:45])[O:46][C@@H:47]3[C@H:54]4[C@H:50]([O:51][CH2:52][CH2:53]4)[O:49][CH2:48]3)[CH2:21][C:18]3[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][N:57]4[CH2:58][CH2:59][S:55][CH2:56]4)=[CH:20][CH:19]=3)(=[O:32])=[O:31])=[CH:34][C:35]=2[O:39][CH2:38]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 10444ThiazolidineHCID 59997347HCID 59997347, compound

Product 1

HCID 59997373HCID 59997373, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(4-{(2S,3R)-2-({[(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-4-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-3-hydroxybutyl}phenoxy)ethyl 4-methylbenzenesulfonate (50 mg, 0.06 mmol), thiazolidine (0.02 mL, 0.02 g, 0.25 mmol) and dimethylsulfoxide (1 mL) was heated to 70° C. under nitrogen atmosphere for 2 h. The mixture was diluted with water and extracted with ethyl ether (2×). The organic phase was dried (sodium sulfate), evaporated, and the residue was purified by chromatography (silica gel, dichloromethane/methanol, 98:2) to provide the title compound (25 mg) as a solid foam. 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.82 (3H, d), 1.2 (1H, dd), 1.4 (1H, quintuplet), 1.9-2.0 (1H, m), 2.3 (1H, dd), 2.6-2.8 (7H, m), 2.8-3.0 (5H, m), 3.4-3.6 (4H, m), 3.7 (1H, t), 3.8 (1H, dd), 4.0 (2H, br s), 4.05 (2H, br s), 4.8 (1H, dt), 5.0 (1H, d), 5.5 (1H, d), 6.18 (2H, s), 6.8 (2H, d), 7.0-7.1 (3H, d), 7.18 (1H, d), 7.2 (1H, s), 7.3 (1H, d); MS: 708 (MH+)

Workup

  1. extractionextracted with ethyl ether (2×)
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. customevaporated
  4. customthe residue was purified by chromatography (silica gel, dichloromethane/methanol, 98:2)

Sources & evidence

ORD record
ord-92a47966607c4c2c892101d2eb6698c3
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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