Formaldehyde → HCID 131728052, compound

HRID 642935Notes

Reaction equation

HRID 642935 reaction equation
[C:1]([Si:5]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[O:6][CH:7]1[C:11]([C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])([C:12]([O:14][N:15]2C(=O)C3C(=CC=CC=3)[CH2:16]2)=O)[O:10][CH:9]([N:44]2[CH:49]=[CH:48][C:47](=[O:50])[NH:46][C:45]2=[O:51])[CH:8]1[O:52]C(=O)C)([CH3:4])([CH3:3])[CH3:2].CNN.CO.C=O>ClCCl>[C:1]([Si:5]([C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[O:6][CH:7]1[C:11]([C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:26][SiH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH2:12][O:14][N:15]=[CH2:16])[O:10][CH:9]([N:44]2[CH:49]=[CH:48][C:47](=[O:50])[NH:46][C:45]2=[O:51])[CH:8]1[OH:52])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 6061MethylhydrazineHCID 178475576HCID 178475576, compound

Product 1

HCID 131728052HCID 131728052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

This transformation is performed smoothly in high yield using published procedures (Bhat, B., et. al., J. Org. Chem. 1996, 61, 8186-8199). Generally, a portion of Compound 16 is dissolved in dichloromethane and cooled to −10° C. To this solution is added methylhydrazine (2.5 eq.). After 1-2 hours of stirring at 0° C., the mixture is diluted with dichloromethane, washed with water and brine, dried with anhydrous Na2SO4, filtered, and evaporated. The resulting residue is immediately redissolved in a 1:1 mixture of ethyl acetate:methanol, and treated with 20% (w/w) aqueous formaldehyde (1.1 eq.). After an hour at room temperature, the mixture is concentrated then purified by silica gel chromatography to give Compound 17.

Workup

  1. customin high yield
  2. washwashed with water and brine
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe resulting residue is immediately redissolved in a 1:1 mixture of ethyl acetate
  7. waitAfter an hour at room temperature
  8. concentrationthe mixture is concentrated
  9. customthen purified by silica gel chromatography

Sources & evidence

ORD record
ord-6a5a689c518747408139321f0f79fb66
Source dataset
uspto-grants-2010_04
Patent number
US07696345B2

Reaction notes

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