Benzyl chloroformate → HCID 67871753, compound

HRID 1457329Notes

Reaction equation

HRID 1457329 reaction equation
[N:1]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([O-:12])=O.[NH:23]1[C:31]2[C:26](=CC=CC=2)[CH2:25][CH:24]1[C:32](O)=[O:33].[OH-].[Na+].C(Cl)(OCC1C=CC=CC=1)=O>O>[C:17]1([CH2:16][O:15][C:13]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH:2]2[C:10]([N:23]2[CH2:31][CH2:26][CH2:25][CH:24]2[CH2:32][OH:33])=[O:12])=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 86074Indoline-2-carboxylic acidHCID 21620025HCID 21620025, compound

Product 1

HCID 67871753HCID 67871753, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-dihydro-1H-indole-1,2-dicarboxylic acid, 1-(phenylmethyl) ester. 10.0 g (0.0612 mol) of indoline-2-carboxylic acid was added to 100 ml of water and 1N NaOH was added to the solution until the pH was 8.0. To the resulting solution, 9.10 ml (0.0637 mol) carbobenzyloxychloride was added dropwise. The reaction mixture was stirred for 1 hour at room temperature while keeping the pH between 7.5 and 8.5 with addition of 1N NaOH. The mixture was then extracted with ether and the ether extracts discarded. The pH of the reaction mixture was then adjusted to 6.3 and extracted with ethyl acetate. The ethyl acetate extracts were combined, dried, and evaporated. The residue was chromatographed on silica gel eluting with 3:7/ethyl acetate:hexane. Fractions containing the desired material were combined and evaporated to yield 9.3 g (51%) of the title compound as a white amorphous solid. TLC (10:1/chloroform:methanol) Rf =0.25. 1H NMR (CDCl3) δ: 6.8-7.9(m,9H); 4.8-5.4(m,3H); 3.50(m,1H); 3.20(m,1H).

Workup

  1. additionwas added to the solution until the pH was 8.0
  2. extractionThe mixture was then extracted with ether
  3. extractionextracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with 3:7/ethyl acetate
  7. additionFractions containing the desired material
  8. customevaporated

Sources & evidence

ORD record
ord-84867f893cc34da2904b347fd8285dd2
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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