Acetic Acid → HCID 68312940, compound

HRID 1472920Notes

Reaction equation

HRID 1472920 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]=1[Cl:20])[CH2:2][CH2:3][CH3:4].[NH2:21][C@@H:22]([CH2:26][OH:27])[CH:23]([CH3:25])[CH3:24].C(O)(=O)C.C([BH3-])#N>CO>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([CH2:18][NH:21][C@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:26][OH:27])[CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]=1[Cl:20])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 6950587D-ValinolHCID 86671316HCID 86671316, compound

Product 1

HCID 68312940HCID 68312940, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 262A (0.500 g, 1.73 mmol) in MeOH (10 mL) at ambient temperature was added D-valinol (0.20 mL, 1.7 mmol), acetic acid (0.40 ml, 6.9 mmol) followed by MP-cyanoborohydride (2.49 mmol/g; 1.00 g). After 2 hours, the mixture was filtered and concentrated. The residue was partitioned between 1N HCl and ethyl acetate. The organic layer was discarded. The aqueous layer made basic with 1N NaOH and extracted with ethyl acetate. The EtOAc extract was dried (Na2SO4) and concentrated to give 420 mg (65%) of the title compound. MS (DCI+) m/z 377 (M+H); 1H NMR (300 MHz, CDCl3) δ 8.03 (d, J=2.3 Hz, 1H), 7.87 (dd, J=8.6, 2.2 Hz, 1H), 7.68 (t, J=7.7 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.17 (d, J=7.6 Hz, 1H), 7.00 (d, J=4.4 Hz, 1H), 4.09 (t, J=6.5 Hz, 2H), 4.06-3.92 (m, 2H), 3.69 (dd, J=10.8, 4.0 Hz, 1H), 3.47 (dd, J=10.8, 6.8 Hz, 1H), 2.51 (td, J=6.7, 4.0 Hz, 1H), 1.95-1.78 (m, 4H), 1.63-1.46 (m, 2H), 0.99 (m, 9H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was partitioned between 1N HCl and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. extractionThe EtOAc extract
  6. dry with materialwas dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e9be8e6aba3b4dd0a0177dbdc158f2d1
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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