Hydrochloric Acid → 239075-86-6

HRID 1954459Notes

Reaction equation

HRID 1954459 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]([OH:30])[C@H:26]([NH2:29])[CH2:27][OH:28])=[CH:21][CH:20]=1)([O-:18])=[O:17].Cl>CCO>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]([OH:30])[C@H:26]([NH2:29])[CH2:27][OH:28])=[CH:23][CH:24]=1)([O-:18])=[O:17].[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69745Chloramphenicol D baseHCID 100587711-Acetyl-2-indolinecarboxylic acid

Product 1

HCID 70287241239075-86-6Yield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

25 g N-acetyl-indoline-2-carboxylic acid (purity 96.5%) was dissolved in 300 ml absolute EtOH while being heated to 70° C. and with mechanical stirring. 17.25 g/0.69 eq. (1R,2R)-1-(4-nitrophenyl)-2-amino-1,3-propanediol (99.5% chemically pure, [a]20D =-28.5° (c=0.4, 1N HCl)) was dosed in portions in 30 min. at 66-70° C. Spontaneous crystallization occurred. After 30 minutes' subsequent stirring at 69-70° C., cooling to 18° C. took place in 2.5 hours, followed by another 30 minutes' stirring. After filtration over a P4 glass filter 3 washings with 30 ml EtOH took place. After air-drying, 20.7 g yellow (S)-N-acetyl-indoline-2-carboxylic acid-(1R,2R)-1-(4-nitrophenyl)-2-amino-1,3-propanediol salt was obtained, corresponding to a yield of 42.0%. Enantiomeric excess=95.9% (chiral HPLC).

Workup

  1. customSpontaneous crystallization
  2. temperaturecooling to 18° C.
  3. customin 2.5 hours
  4. waitfollowed by another 30 minutes
  5. stirring' stirring
  6. filtrationAfter filtration over a P4 glass
  7. filtrationfilter
  8. wash3 washings with 30 ml EtOH
  9. customAfter air-drying

Sources & evidence

ORD record
ord-7102cb6b14e044b8b77e67df03e6c050
Source dataset
uspto-grants-2000_09
Patent number
US06121460

Reaction notes

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