Hydrochloric Acid → HCID 178508898, compound

HRID 1639246Notes

Reaction equation

HRID 1639246 reaction equation
[OH:1][CH2:2][CH:3]([C:23]1[CH:44]=[CH:43][C:26]([C:27]([NH:29][C@H:30]([C:38]([O:40]CC)=[O:39])[CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[O:28])=[CH:25][CH:24]=1)[CH2:4][CH:5]1[CH2:22][NH:21][C:8]2[N:9]=[C:10]([NH:14]C(=O)C(C)(C)C)[N:11]=[C:12]([OH:13])[C:7]=2[CH2:6]1.Cl>[OH-].[Na+]>[OH:1][CH2:2][CH:3]([C:23]1[CH:44]=[CH:43][C:26]([C:27]([NH:29][C@H:30]([C:38]([OH:40])=[O:39])[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:28])=[CH:25][CH:24]=1)[CH2:4][CH:5]1[CH2:22][NH:21][C:8]2[N:9]=[C:10]([NH2:14])[N:11]=[C:12]([OH:13])[C:7]=2[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178471573HCID 178471573, compound

Product 1

HCID 178508898HCID 178508898, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 300 mg (0.49 mm) of diethyl N-[4-{1-hydroxy-3-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamate in 9 ml of 1N aqueous sodium hydroxide was stirred under nitrogen at ambient temperature for 72 hours. The reaction mixture was rendered slightly acidic (pH=~4) with 1N hydrochloric acid and filtered. The solid thus collected was washed with water (5 ml) and cold ethanol (5 ml) and dried to give 180 mg (78%) of N-[4-{1-hydroxy-3-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl}benzoyl]glutamic acid. mp 275° C. (dec.). Analysis calculated for C22H27N5O7.0.5H2O: C, 54.76; H, 5.80; N, 14.51. Found: C, 54.96; H, 5.88; N, 14.27. NMR (DMSOd6, CF3COOD), delta, 1.35-1.42 (m, 1H), 1.58-1.71 (m, 2H), 1.73-1.85 (m, 1H), 1.86-2.01 (m, 1H), 2.02-2.13 (m, 1H), 2.31 (t, 2H, J=7 Hz), 2.39-2.52 (m, 1H), 2.74-2.89 (m, 2H), 3.08-3.14 and 3.24-3.30 (m, m, 1H), 3.47 (d, 2H, J=3.7 Hz), 4.37 (dd, 1H, J=19.4 Hz, J=4.7 Hz), 7.27-7.30 (m, 2H), 7.78 (d, 2H, J=7.7 Hz).

Workup

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

Sources & evidence

ORD record
ord-37e8c9f181ce4ff994bcbe9d82742d0e
Source dataset
uspto-grants-1989_11
Patent number
US04883799

Reaction notes

Loading…