Methanol → HCID 67126399, compound

HRID 1036012Notes

Reaction equation

HRID 1036012 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C@H:10]1[O:15][CH2:14][CH2:13][NH:12][CH2:11]1.CO.C(O[C:25]1(O[Si](C)(C)C)[CH2:27][CH2:26]1)C.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:16]([NH2:19])(=[O:18])=[O:17])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C@H:10]1[O:15][CH2:14][CH2:13][N:12]([CH:25]2[CH2:27][CH2:26]2)[CH2:11]1

Participants

6

Reactant 4

HCID 887MethanolHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride2×HCID 67169690HCID 67169690, compound

Product 1

HCID 67126399HCID 67126399, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of EXAMPLE 244B (250 mg), anhydrous methanol (6 mL), (1-ethoxycyclopropoxy)trimethylsilane (0.474 mL), and acetic acid (0.509 mL) was heated at 70° C. for 30 minutes. After cooling to ambient temperature, sodium cyanoborohydride (112 mg) was added and the mixture was stirred for 18 hours. Additional sodium cyanoborohydride (75 mg) was added and stirring was continued 18 hours. The reaction was concentrated and the residue was partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product was isolated from the dried methylene chloride layer and was purified on silica gel and was eluted with a 1, 2.5, 5, 10% methanol in methylene chloride step gradient to provide the title compound.

Workup

  1. stirringstirring
  2. waitwas continued 18 hours
  3. concentrationThe reaction was concentrated
  4. customthe residue was partitioned between methylene chloride and saturated sodium bicarbonate solution
  5. customThe crude product was isolated from the dried methylene chloride layer
  6. customwas purified on silica gel
  7. washwas eluted with a 1, 2.5, 5, 10% methanol in methylene chloride step gradient

Sources & evidence

ORD record
ord-bcda9c8e8813450e8cab11c819ecb719
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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