Hydrochloric Acid → Pemetrexed

HRID 263708Notes

Reaction equation

HRID 263708 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:27][CH2:28][C:29]([O:31]C)=[O:30])[NH:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[C:23]3[C:22](=[O:24])[NH:21][C:20]([NH2:25])=[N:19][C:18]=3[NH:17][CH:16]=2)=[CH:9][CH:8]=1.[OH-].[Na+].Cl>>[NH2:25][C:20]1[NH:21][C:22](=[O:24])[C:23]2[C:15]([CH2:14][CH2:13][C:10]3[CH:9]=[CH:8][C:7]([C:6]([NH:5][C@H:4]([C:3]([OH:33])=[O:2])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:12][CH:11]=3)=[CH:16][NH:17][C:18]=2[N:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1361208391,5-Dimethyl N-(4-(2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-L-glutamate

Product 1

HCID 135410875PemetrexedYield 59%

Procedure

A mixture of 0.50 g (1.1 mmol) of N-[4-[2-[2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]ethyl]benzoyl]glutamic acid dimethyl ester, prepared in Preparation 5, and 3.3 ml of 2N aqueous sodium hydroxide was stirred at room temperature for 48 hours and neutralized to a pH of 5 with 6M aqueous hydrochloric acid. The precipitate was filtered, washed with water and dried, to give 0.277 g of the above product in a yield of 59 percent.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-037d8de6cdd242608cec0ecc6a86f029
Source dataset
uspto-grants-1997_07
Patent number
US05644058

Reaction notes

Loading…