Hydrochloric Acid → HCID 178508897, compound

HRID 1639014Notes

Reaction equation

C([NH:7][C:8]1[N:9]=[C:10]([OH:37])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][C@H:26]([C:33]([O:35]C)=[O:34])[CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[O:24])[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:37])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][C@H:26]([C:33]([OH:35])=[O:34])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:24])[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 178500486HCID 178500486, compound

Product 1

HCID 178508897HCID 178508897, compound

Procedure

A solution of 0.5 g. of dimethyl N-[6-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d] -pyrimidin-6-yl)hexanoyl]-L-glutamate in 75 mL. of 1.0 N aqueous sodium hydroxide is stirred at room temperature for 120 hours and the pH then adjusted to 7.0 through the careful addition of 5.0 N hydrochloric acid. Water was removed under reduced pressure and the concentrated solution then cooled in an ice-bath. The solid which formed was collected by filtration and dried at 80° C. to yield N-[6-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido-[2,3-d]pyrimidin-6-yl)hexanoyl]-L-glutamic acid, m.p. foaming at 135° C., melting at 180°-195° C. NMR (DMSO-d6 300 MHz) delta: 9.80 (s, br, 1H), 7.90 (s, J=8 Hz, 1H), 6.20 (s, 1H), 5.95 (s, 2H), 4.08 (m, 1H), 3.10 (m, 1H), 2.63 (t, J=10 Hz, 1H), 2.40 (m, 1H), 2.20 (t, J=8 Hz, 2H), 2.05 (t, J=8 Hz, 2H), 1.84 (m, 1H), 1.70 (m, 2H), 1.55 (m, 3H), 1.20 (m, 6H).

Workup

customWater was removed under reduced pressure
temperaturethe concentrated solution then cooled in an ice-bath
customThe solid which formed
filtrationwas collected by filtration
customdried at 80° C.

Sources & evidence

ORD record: ord-ac121774285c496a975b86a9e94ad3ac
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04882333

Reaction notes

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