Sodium borohydride → HCID 178471764, compound

HRID 2042721Notes

Reaction equation

HRID 2042721 reaction equation
[BH4-].[Na+].[C:3]12([C:13](=[O:39])[CH2:14][O:15][C:16]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([C@H:27]5[CH2:32][CH2:31][C@H:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[NH:18][N:17]=3)[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>O1CCCC1.C(O)C>[C:3]12([CH:13]([OH:39])[CH2:14][O:15][C:16]3[CH:20]=[C:19]([C:21]4[CH:22]=[CH:23][C:24]([C@H:27]5[CH2:28][CH2:29][C@H:30]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:31][CH2:32]5)=[CH:25][CH:26]=4)[NH:18][N:17]=3)[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178471763HCID 178471763, compound

Product 1

HCID 178471764HCID 178471764, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (38 mg, 0.1 mmol) was added to a solution of the product from Example 1F (25 mg, 0.05 mmol) in tetrahydrofuran (3 mL) and ethanol (3 mL) maintained at 0° C. The reaction was allowed to warm to room temperature over 30 min and then stirred at room temperature for 1 hour. After this time the reaction was quenched by addition of water (5 mL) and extracted with ethyl acetate. The organic extracts were combined and washed with water, brine, dried (MgSO4), filtered and concentrated to a brown oil which was purified via flash column (eluting with 15% ethyl acetate in hexanes) to provide the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.12 (m, 2H), 1.19 (t, J=7.32 Hz, 3H), 1.42-1.99 (m, 22H), 2.22 (d, J=6.71 Hz, 2H), 2.47 (m, 1H), 3.89 (dd, J1=10.38 Hz, J2=7.94 Hz, 1H), 4.02 (m, 1H), 4.06 (q, J=7.32 Hz, 2H), 4.24 (dd, J1=10.37 Hz, J2=2.74 Hz, 1H), 4.71 (s, 1H), 6.07 (s, 1H), 7.28 (d, J=8.24 Hz, 2H), 7.59 (d, J=8.24 Hz, 2H), 12.21 (br s, 1H); MS (ESI) m/z 507.4 [M+H]+.

Workup

  1. temperatureto warm to room temperature over 30 min
  2. customAfter this time the reaction was quenched by addition of water (5 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a brown oil which
  8. customwas purified via flash column (eluting with 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-66aaf0f2f61c4d93931cb14af2c0de96
Source dataset
uspto-grants-2013_11
Patent number
US08586594B2

Reaction notes

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