Hydrochloric Acid → HCID 178508887, compound

HRID 1638995Notes

Reaction equation

HRID 1638995 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[S:24][C:23]([C:25]([NH:27][C@H:28]([C:35]([O:37]C)=[O:36])[CH2:29][CH2:30][C:31]([O:33]C)=[O:32])=[O:26])=[CH:22][CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.[OH-].[Na+].Cl>>[NH2:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[S:24][C:23]([C:25]([NH:27][C@H:28]([C:35]([OH:37])=[O:36])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])=[CH:22][CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178500480HCID 178500480, compound

Product 1

HCID 178508887HCID 178508887, compoundYield 76.8%

Procedure

A solution of 100 mg. of dimethyl N-[5-(2-{2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl}ethyl)thien-2-ylcarbonyl]-L-glutamate in 15 mL. of 1.0N aqueous sodium hydroxide is stirred at room temperature for 120 hours and the pH then adjusted to 7.0 through the careful addition of 5.0N hydrochloric acid. The solid which formed was collected by filtration and dried at 80° C. to yield 61.5 mg (76.8%) of N-[5-(2-{2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl}ethyl)thien-2-ylcarbonyl]-L-glutamic acid, m.p. 226°-240° C. (foaming and decomposition). NMR (DMSO-d6 300 MHz) delta: 9.80 (s, br, 1H), 8.45 (d, J=9 Hz, 1H), 7.62 (d, J=3 Hz, 1H), 6.87 (d, J=3 Hz, 1H), 6.30 (s, 1H), 6.04 (s, 2H), 4.28 (m, 1H), 3.12 (m, 1H), 2.84 (m, 3H), 2.36 (m, 1H), 2.02 (m, 1H), 1.83 (m, 2H), 1.57 (m, 3H).

Workup

  1. customThe solid which formed
  2. filtrationwas collected by filtration
  3. customdried at 80° C.

Sources & evidence

ORD record
ord-574cb4de2792428fb9e2f795883a84d9
Source dataset
uspto-grants-1989_11
Patent number
US04882334

Reaction notes

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