Methanol → HCID 66774323, compound

HRID 1629685Notes

Reaction equation

HRID 1629685 reaction equation
[OH:1][CH:2]1[CH:12]2[CH:5]([CH2:6][O:7][Si:8]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[O:9][Si:10]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:11]2)[O:4][CH:3]1[N:25]1[CH:30]=[CH:29][C:28](=[O:31])[NH:27][C:26]1=[O:32].[C:33](OC(=O)C)(=[O:35])[CH3:34].C(N(CC)CC)C.CO>N1C=CC=CC=1>[O:32]=[C:26]1[NH:27][C:28](=[O:31])[CH:29]=[CH:30][N:25]1[CH:3]1[O:4][CH:5]2[CH2:6][O:7][Si:8]([CH:22]([CH3:23])[CH3:24])([CH:19]([CH3:21])[CH3:20])[O:9][Si:10]([CH:16]([CH3:17])[CH3:18])([CH:13]([CH3:14])[CH3:15])[O:11][CH:12]2[CH:2]1[O:1][C:33](=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13406056HCID 13406056, compound2×

Product 1

HCID 66774323HCID 66774323, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 4 is O-Acetylated using well known literature procedures (Protective Groups in Organic Synthesis, 3rd edition, 1999, pp. 150-160 and references cited therein and in Greene, T. W. and Wuts, P. G. M., eds, Wiley-Interscience, New York.) Acetic anhydride (2 to 2.5 eq.) and triethylamine (4 eq.) is added to a solution of 4 (1 eq.) and N,N-dimethylaminopyridine (0.1 eq.) in anhydrous pyridine. After stirring at room temperature for 1 hour the mixture is treated with methanol to quench excess acetic anhydride and evaporated. The residue is redissolved in ethyl acetate, washed extensively with aqueous NaHCO3, dried over anhydrous Na2SO4, filtered, and evaporated. The compound is used without further purification.

Workup

  1. customin Organic Synthesis, 3rd edition, 1999
  2. customto quench excess acetic anhydride
  3. customevaporated
  4. dissolutionThe residue is redissolved in ethyl acetate
  5. washwashed extensively with aqueous NaHCO3
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe compound is used without further purification

Sources & evidence

ORD record
ord-f8244bde9a57471e90d9084bb69e4799
Source dataset
uspto-grants-2014_07
Patent number
US08791083B2

Reaction notes

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