Acetic Acid → HCID 90412289, compound

HRID 1521961Notes

Reaction equation

HRID 1521961 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:21][CH2:20][NH:19][CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1.C(N(CC)CC)C.C(O)(=O)C.[Si:35]([O:42][CH2:43][CH:44]=O)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].C([BH3-])#N>ClCCl.CO>[Si:35]([O:42][CH2:43][CH2:44][N:19]1[CH2:20][CH2:21][CH:17]([C:15]2[NH:14][C:10]3=[N:11][CH:12]=[CH:13][C:8]([C:6]4[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[O:22][CH3:23])=[C:9]3[CH:16]=2)[CH2:18]1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 498716Cyano-borohydrideHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 90412361HCID 90412361, compound

Product 1

HCID 90412289HCID 90412289, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 59F (50 mg, 0.130 mmol) in dichloromethane (1 mL)/methanol (1 mL) was added triethylamine (0.036 mL, 0.260 mmol) followed by acetic acid (0.037 mL, 0.651 mmol) and (t-butyldimethylsilyloxy)acetaldehyde (0.050 mL, 0.260 mmol). After stirring for 5 minutes, MP-cyanoborohydride (2.49 mmol/g, 209 mg, 0.52 mmol) was added and the mixture was shaken for 16 hours at room temperature. The resin was filtered off, and washed with methanol/dichloromethane (2×3 mL). The crude mixture was concentrated and used in the next step without further purification. LCMS: 470.3 (M+H)+.

Workup

  1. stirringthe mixture was shaken for 16 hours at room temperature
  2. filtrationThe resin was filtered off
  3. washwashed with methanol/dichloromethane (2×3 mL)
  4. concentrationThe crude mixture was concentrated
  5. customused in the next step without further purification

Sources & evidence

ORD record
ord-110365567a4f4a52955b2a2d4260c2e1
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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