Tetrahydrofuran → 3-Tetradecylthioacetylamino-1-tetradecylthiacetyloxy-2-tetradecylthioacetylthiopropane

HRID 853206Notes

Reaction equation

HRID 853206 reaction equation
[CH2:1]([CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH:21]([S:23][C:24](=[S:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[OH:22])=[S:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1(N=C=N[CH:50]2[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]2)CCCCC1.CN([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61]N=1)C.[CH2:65]([CH2:79][C:80](O)=[S:81])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77]C.O1C[CH2:86][CH2:85][CH2:84]1>>[CH2:1]([CH2:15][C:16]([NH:18][CH2:19][CH2:20][C:21]([O:22][S:81][CH2:80][CH2:79][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77])([S:23][C:24](=[S:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:59][CH2:64][CH2:63][CH2:62][CH2:61][CH2:84][CH2:85][CH2:86][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:50])=[S:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 866032123-Tetradecylthioacetylamino-2-tetradecylthioacetylthiopropan-1-olHCID 178443127HCID 178443127, compound

Product 1

HCID 866032143-Tetradecylthioacetylamino-1-tetradecylthiacetyloxy-2-tetradecylthioacetylthiopropaneYield 17%

Procedure

3-tetradecylthioacetylamino-2-tetradecylthioacetylthiopropan-1-ol (example 20) (64 mg, 0.10 mmol) was dissolved in tetrahydrofuran (7 ml). Dicyclohexylcarbodiimide (31 mg, 0.15 mmol), dimethylaminopyridine (18 mg, 0.15 mmol) and tetradecylthioacetic acid (example 1) (43 mg, 0.15 mmol) were then added. The mixture was stirred at room temperature for 20 hours. The dicyclohexylurea precipitate was filtered and the filtrate was evaporated. The residue obtained (140 mg) was purified by flash chromatography (eluent: dichloromethane) to give the desired compound in the form of a white powder.

Workup

  1. filtrationThe dicyclohexylurea precipitate was filtered
  2. customthe filtrate was evaporated
  3. customThe residue obtained (140 mg)
  4. customwas purified by flash chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-c22d517af3b2487f9866d9f291e38adc
Source dataset
uspto-grants-2007_08
Patent number
US07253296B2

Reaction notes

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