Ammonia → HCID 11245365, compound

HRID 2223009Notes

Reaction equation

HRID 2223009 reaction equation
[OH:1][C@H:2]([CH2:6][O:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]#[N:5].N.[OH:28]O>C(O)C>[OH:1][C@H:2]([CH2:6][O:7][C:8]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][C:4]([NH2:5])=[O:28]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 11210088HCID 11210088, compound

Product 1

HCID 11245365HCID 11245365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirring solution of (S)-3-hydroxy-4-trityloxybutanenitrile (5.15 g, 15.01 mmol) in 15 mL of ethanol at room temperature was added aqueous NH3 (50 mL) and H2O2 (100 vol.) (34 mL, 300.00 mmol) was added in portions while maintaining the temperature of the reaction mixture below 25° C. After complete addition, the resultant reaction mixture was stirred vigorously at 25-30° C. and the reaction progress was monitored by TLC. On completion of the reaction (overnight) as indicated by the TLC, the reaction volume was concentrated to about 50% of the original volume under reduced pressure and the resultant mixture was extracted with dichloromethane (3×75 mL). The combined organic layers were dried over anhydrous Na2SO4 and the solvent was evaporated to leave a residue, which was purified by column chromatography employing EtOAc-hexane (80:20) as eluent to afford (S)-3-hydroxy-4-trityloxy butanamide in almost quantitative yield. m.p. 96-100° C.; [α]27D=−18.08 (c 1.0, MeOH); IR (KBr) 3467, 3349, 3012, 2980, 2918, 2839, 1671, 1098, 1076 cm−1; 1HNMR (300 MHz, CDCl3) δ 2.36 (d, 2H, J=6.5 Hz), 3.13-3.16 (m, 2H), 3.28 (6S, 1H), 4.11-4.15 (m, 1H), 5.44 (br, s, 1H), 7.18-7.38 (m, 9H), 7.39-7.42 (m, 6H); Mass (EI) 361, 259, 243, 165, 77.

Workup

  1. additionwas added in portions
  2. temperaturewhile maintaining the temperature of the reaction mixture below 25° C
  3. additionAfter complete addition
  4. customthe resultant reaction mixture
  5. customOn completion of the reaction (overnight)
  6. concentrationthe reaction volume was concentrated to about 50% of the original volume under reduced pressure
  7. extractionthe resultant mixture was extracted with dichloromethane (3×75 mL)
  8. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  9. customthe solvent was evaporated
  10. customto leave a residue, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-bf67b0b762c04ab28f743b8feb721a44
Source dataset
uspto-grants-2008_05
Patent number
US07374926B2

Reaction notes

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