Acetic Acid → HCID 10390885, compound

HRID 1294740Notes

Reaction equation

HRID 1294740 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[CH:5]1([NH:11][C:12]2[CH:13]=[C:14]([C@@H:18]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:19]3[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH:5]1([NH:11][C:12]2[CH:13]=[C:14]([C@@H:18]([N:32]3[CH2:37][CH2:36][N:35]([CH2:1][CH2:2][CH3:3])[CH2:34][CH2:33]3)[C:19]3[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 10049347HCID 10049347, compound

Product 1

HCID 10390885HCID 10390885, compoundYield 61,498.199%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a room temperature solution of propionaldehyde (40.6 μL 0.56 mmol) and COMPOUND 27 (250 mg; 0.56 mmol) in 1,2-dichloroethane was added sodium triacetoxy borohydride (380 mg; 1.79 mmol) and acetic acid (31.9 μL; 0.56 mmol). The reaction mixture was stirred overnight then was washed with saturated sodium bicarbonate, followed by water. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography eluting with 5% methanol in dichloromethane gave COMPOUND 73 (169 g; 62% yield). Purity (HPLC-215 nm): >99%; Optical purity (Chiral HPLC-215 nm): >99%. 1H NMR (400 MHz, CD3OD) δ 0.99 (t, J=7.91 Hz, 2H), 1.10-1.16 (m, 3H), 1.28-1.33 (m, 4H), 1.61-1.65 (m, 4H), 1.75-1.79 (m, 4H), 1.83-1.90 (m, 4H), 2.97-3.01 (m, 2H), 3.13-3.15 (m, 2H), 3.17-3.28 (m, 8H), 3.42-3.46 (m, 2H), 3.52-3.54 (m, 1H), 5.08 (s, 1H) 7.24-7.29 (m, 3H), 7.48-7.51 (m, 3H), 7.55-7.57 (m, 1H), 7.62 (d, J=7.42 Hz, 1H). Found: C, 56.59; H, 7.89; N, 8.25. C31H46N4O×4.3HCl×0.6H2O has C, 56.56; H, 7.89; N, 8.51%. [α]D16=+14.5 deg [c 0.50, MeOH].

Workup

  1. washthen was washed with saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washColumn chromatography eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-b59beae213f048d7b0df598e4aeeee6b
Source dataset
uspto-grants-2007_07
Patent number
US07241764B2

Reaction notes

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