Hydrochloric Acid → HCID 58720356, compound

HRID 1246001Notes

Reaction equation

HRID 1246001 reaction equation
[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:34])[C@H:23]([CH2:25][CH2:26][C:27](=[O:33])[O:28]C(C)(C)C)[NH2:24])[CH:16]=1)=[CH:8][CH:7]=2)(=[O:3])[NH2:2].Cl>C(Cl)Cl.O1CCOCC1>[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:34])[C@H:23]([CH2:25][CH2:26][C:27](=[O:28])[OH:33])[NH2:24])[CH:16]=1)=[CH:8][CH:7]=2)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58720365HCID 58720365, compound

Product 1

HCID 58720356HCID 58720356, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Carbamoyl-5-[3-(O-tert-butyl-α-glutamylamino)benzyloxy]-1H-indole (0.29 g; 0.62 mmol) in solution in CH2Cl2 (2 ml) was treated under argon with HCl (2N) in dioxan (4 ml). The mixture was stirred for one hour, evaporated and the residue was purified on OASIS resin, eluting with H2O/CH3CN 80/20 to give 2-carbamoyl-5-[3-(α-glutamylamino)benzyloxy]-1H-indole.

Workup

  1. customevaporated
  2. customthe residue was purified on OASIS resin
  3. washeluting with H2O/CH3CN 80/20

Sources & evidence

ORD record
ord-6cf77043b7d4418ba42799bce880ee95
Source dataset
uspto-grants-2006_10
Patent number
US07125906B2

Reaction notes

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