Isobutyraldehyde → HCID 59784097, compound

HRID 2079764Notes

Reaction equation

HRID 2079764 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:39])[C:11]([NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C@H:21]1[C:26]([NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:27])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH:40](=O)[CH:41]([CH3:43])[CH3:42].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH2:40]([N:23]1[CH2:24][CH2:25][N:20]([C:18]([C@@H:14]([NH:13][C:11](=[O:12])[C@@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:7])([CH3:8])[CH3:6])[CH3:39])[CH:15]([CH3:17])[CH3:16])=[O:19])[C@H:21]([C:26]([NH:28][C@H:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:32][CH2:31][CH2:30]2)=[O:27])[CH2:22]1)[CH:41]([CH3:43])[CH3:42]

Participants

6

Reactant 3

HCID 6561Isobutyraldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 59784098HCID 59784098, compound

Product 1

HCID 59784097HCID 59784097, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Intermediate 7 (250 mg, 0.46 mmol) is dissolved in 1,2-dichloroethane (4 mL), to which is added iso-butyraldehyde (63 μL, 0.69 mmol) and NaBH(OAc)3 (146 mg, 0.69 mmol). This mixture is stirred under N2 at RT overnight. LCMS at this point shows a small amount of unreacted starting material so further quantities of iso-butyraldehyde (63 μL, 0.69 mmol) and NaBH(OAc)3 (146 mg, 0.69 mmol) are added. After a further 4 h. of stirring at RT the reaction mixture is diluted with CH2Cl2 (50 mL) and then washed with water (50 mL), brine (50 mL) and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure to afford an oil which is purified by flash chromatography on silica gel (10-50% Et2O/CH2Cl2). The title compound is isolated as a white foam (255 mg, 92% yield): 1H NMR δ (CDCl3) 6.72-7.27 (m, 5H), 4.37-5.24 br m, 5H), 3.26-3.90 (br m, 2H), 2.67-2.96 (br m, 6H), 1.62-2.19 (m, 1H), 1.48 (s, 9H), 1.23-1.34 (m, 3H), 0.69-0.99 (m, 12H); LCMS (APCl+) 601.3 (MH+, 100%).

Workup

  1. additionare added
  2. stirringAfter a further 4 h. of stirring at RT the reaction mixture
  3. washwashed with water (50 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent is removed under reduced pressure
  7. customto afford an oil which
  8. customis purified by flash chromatography on silica gel (10-50% Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-7f2097e80fbc4fb3bdf8a3b8318e7bdf
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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