Hydrochloric Acid → 239075-86-6

HRID 1954458Notes

Reaction equation

HRID 1954458 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].CCO.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([OH:33])[C@H:29]([NH2:32])[CH2:30][OH:31])=[CH:24][CH:23]=1)([O-:21])=[O:20].Cl>CO.O>[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([C@@H:28]([OH:33])[C@H:29]([NH2:32])[CH2:30][OH:31])=[CH:26][CH:27]=1)([O-:21])=[O:20].[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 69745Chloramphenicol D baseHCID 100587711-Acetyl-2-indolinecarboxylic acid

Product 1

HCID 70287241239075-86-6Yield 40.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
76 °C

Procedure

200 g N-acetyl-indoline-2-carboxylic acid (purity 96.5%) was dissolved in 1760 ml of a mixture containing 90% EtOH, 5% water and 5% MeOH, with heating to 76° C., and with mechanical stirring. 138 g/0.69 eq (1R,2R)-1-(4-nitrophenyl)-2-amino-1,3-propanediol (99.5% chemically pure, [a]20 D =-28.5° (c=0.4, 1N HCl)) was dosed in portions in 30 min. at 73-76° C. After cooling to 70° C., grafting with 1 g S-salt took place, followed by cooling to 15° C. in 3 hours and 30 minutes' subsequent stirring. After filtration over a P4 glass filter, 3 washings with 200 ml EtOH took place. After air-drying, 158.1 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 40.3%. Enantiomeric excess=99.0% (chiral HPLC).

Workup

  1. temperatureAfter cooling to 70° C.
  2. temperatureby cooling to 15° C. in 3 hours and 30 minutes' subsequent stirring
  3. filtrationAfter filtration over a P4 glass
  4. filtrationfilter
  5. wash3 washings with 200 ml EtOH
  6. customAfter air-drying

Sources & evidence

ORD record
ord-5f80c440d26d426aa9dd0350741f9672
Source dataset
uspto-grants-2000_09
Patent number
US06121460

Reaction notes

Loading…