Hydrochloric Acid → HCID 178507208, compound

HRID 2226022Notes

Reaction equation

HRID 2226022 reaction equation
[OH:1][CH2:2][CH:3]([C:22]1[CH:43]=[CH:42][C:25]([C:26]([NH:28][C@H:29]([C:37]([O:39]CC)=[O:38])[CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])=[O:27])=[CH:24][CH:23]=1)[CH2:4][N:5]1[C:10]([OH:11])=[C:9]2[CH:12]=[C:13]([NH:15]C(=O)C(C)(C)C)[N:14]=[C:8]2[N:7]=[CH:6]1.Cl>[OH-].[Na+]>[OH:1][CH2:2][CH:3]([C:22]1[CH:43]=[CH:42][C:25]([C:26]([NH:28][C@H:29]([C:37]([OH:39])=[O:38])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:27])=[CH:24][CH:23]=1)[CH2:4][N:5]1[C:10]([OH:11])=[C:9]2[CH:12]=[C:13]([NH2:15])[N:14]=[C:8]2[N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178471574HCID 178471574, compound

Product 1

HCID 178507208HCID 178507208, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.3 g of diethyl N-[4-{1-hydroxy-3-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidin-3-yl)prop-2-yl}benzoyl]glutamate in 9 ml of 1N aqueous sodium hydroxide is stirred under nitrogen at ambient temperature for 72 hours. The reaction mixture is rendered slightly acidic (pH=-4) with 1N hydrochloric acid and filtered. The solid thus collected is washed with water (5 ml) and cold ethanol (5 ml) and dried to give N-[4-(1-hydroxy-3-(4-hydroxy-6-aminopyrrolo[2,3-d]-pyrimidin-3-yl)prop-2-yl)benzoyl]glutamic acid.

Workup

  1. filtrationfiltered
  2. customThe solid thus collected
  3. washis washed with water (5 ml) and cold ethanol (5 ml)
  4. customdried

Sources & evidence

ORD record
ord-0846c72350b540829bc5318471b9415d
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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