Hydrochloric Acid → (S)-1-Acetylindoline-2-carboxylic acid

HRID 1954460Notes

Reaction equation

HRID 1954460 reaction equation
[N+](C1C=CC([C@@H](O)[C@H](N)CO)=CC=1)([O-])=O.[C:16]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][C@H:20]1[C:28]([OH:30])=[O:29])(=[O:18])[CH3:17].Cl>>[C:16]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][C@H:20]1[C:28]([OH:30])=[O:29])(=[O:18])[CH3:17]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 70287241239075-86-6

Product 1

HCID 11542998(S)-1-Acetylindoline-2-carboxylic acidYield 96.5%

Conditions

Temperature
60 °C

Procedure

1.835 kg dried (S)-N-acetyl-indoline-2-carboxylic acid-(1R,2R)-1-(4-nitrophenyl)-2-amino-1,3-propanediol salt was dosed in portions to 2.64 1 2N HCl aq (1.13 eq HCl) with heating to 60° C., followed by 30 minutes' stirring at 60-70° C. After cooling to 20° C., filtration on an FIBA, washing with 2×0.7 1 water and drying, 871 g white (S)-N-acetyl-indoline-2-carboxylic acid was obtained, corresponding to a yield of 96.5%. Enantiomeric excess=99.9% (chiral HPLC).

Workup

  1. temperatureAfter cooling to 20° C.
  2. filtrationfiltration on an FIBA
  3. washwashing with 2×0.7 1 water
  4. customdrying

Sources & evidence

ORD record
ord-7a49ddb79dbe4c608a7bdc4e0ebf9fda
Source dataset
uspto-grants-2000_09
Patent number
US06121460

Reaction notes

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