Triethylamine → HCID 123486832, compound

HRID 1757706Notes

Reaction equation

HRID 1757706 reaction equation
[CH3:1][O:2][C:3]1[CH:57]=[CH:56][C:6]([C:7]([O:22][CH2:23][C@@:24]2([CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][N:53]=[N+]=[N-])[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[O:38][SiH2:39][C:40]([CH3:45])([CH3:44])[CH:41]([CH3:43])[CH3:42])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:65][C:66]([F:73])([F:72])[C:67](OCC)=[O:68]>CO.ClCCl>[CH3:1][O:2][C:3]1[CH:57]=[CH:56][C:6]([C:7]([O:22][CH2:23][C@@:24]2([CH:46]=[CH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][NH:53][C:67](=[O:68])[C:66]([F:73])([F:72])[F:65])[O:28][C@@H:27]([N:29]3[CH:37]=[C:35]([CH3:36])[C:33](=[O:34])[NH:32][C:30]3=[O:31])[CH2:26][C@@H:25]2[O:38][SiH2:39][C:40]([CH3:45])([CH3:44])[CH:41]([CH3:43])[CH3:42])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 9794Ethyl trifluoroacetateHCID 123511801HCID 123511801, compound

Product 1

HCID 123486832HCID 123486832, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To Compound (5) (450 mg, 0.56 mmole) in dry methanol (7.5 mL) was added under stirring 1,3-propanedithiol (0.284 mL, 2.82 mmole) followed by triethylamine (0.394 mL, 2.82 mmole). The mixture was stirred at room temperature for 5 days. The mixture was diluted with methanol (7 mL) and ethyl trifluoroacetate (0.675 mL, 5.6 mole) and triethylamine (0.237 mL, 1.7 mole) was added. Stirring at room temperature was continued for 24 hours. The resulting suspension was diluted with dichloromethane (5 mL) and the solvent was removed under reduced pressure. Column chromatography on silica gel with ethyl acetate/hexane mixtures gave 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(dimethyl-1,1-dimethylethyl)silyl]-4'-(7-trifluoroacetamido-1-hepten-1-yl)-thymidine (6) (371 mg, 76%), m.p. 75°-76° C.

Workup

  1. additionwas added
  2. stirringStirring at room temperature
  3. waitwas continued for 24 hours
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-67e121932f6342998547749f0d620dda
Source dataset
uspto-grants-1995_08
Patent number
US05446137

Reaction notes

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