Acetic Acid → HCID 11698244, compound

HRID 1726008Notes

Reaction equation

HRID 1726008 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)=O.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:33][C:34]1[CH:43]=[CH:42][C:41]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=2[C:35]=1[C:44]([O:46][CH3:47])=[O:45])(=[O:32])=[O:31].C(O)(=O)C.C([BH3-])#[N:53]>CC(N(C)C)=O.C(Cl)Cl.CO>[NH:53]1[CH2:8][CH2:7][CH2:6][C@H:11]1[CH2:10][CH2:9][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:33][C:34]1[CH:43]=[CH:42][C:41]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=2[C:35]=1[C:44]([O:46][CH3:47])=[O:45])(=[O:32])=[O:31]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 159087TriacetoxyperiodinaneHCID 498716Cyano-borohydrideHCID 11581279HCID 11581279, compound

Product 1

HCID 11698244HCID 11698244, compound

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of Example 552A (0.546 g, 2.5 mmol) in dimethylacetamide (14 mL) was treated with Dess-Martin periodinane (8.25 mL of 15 wt % solution in CH2Cl2, 2.1 mmol) stirred for 15 minutes, and filtered. The filtrate was added to a solution of Example 552C (1.005 g, 2.79 mmol) in CH2Cl2/methanol (11 mL) and the resulting mixture was treated with acetic acid (1.65 mL) and macroporous polystyrene bound cyanoborohydride resin (3.3 g, 7.5 mmol), shaken at 70° C. for 15 hours, filtered, concentrated, and purified by flash chromatography eluting with 30% ethyl acetate/hexanes. The purified product was dissolved in CH2Cl2 (100 mL), treated with TFA (20 mL), stirred for 1.5 hours, and concentrated to provide the desired product. MS (DCI) m/e 444 (M+H)+.

Workup

  1. filtrationfiltered
  2. stirringshaken at 70° C. for 15 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography
  6. washeluting with 30% ethyl acetate/hexanes
  7. dissolutionThe purified product was dissolved in CH2Cl2 (100 mL)
  8. additiontreated with TFA (20 mL)
  9. stirringstirred for 1.5 hours
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8eb1e62dcc904e50bef394000746b1bb
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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