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Sodium cyanoborohydride → HCID 135577948, compound

HRID 2165721
Notes
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Reaction equation

HRID 2165721 reaction equation
[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH:19]=O)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2].[NH2:22][C:23]1[CH:42]=[CH:41][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]([NH:4][C:5]1[NH:6][C:7](=[O:21])[C:8]([CH2:18][CH2:19][NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][C@H:30]([C:37]([O:39][CH3:40])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:28])=[CH:41][CH:42]=2)=[C:9]([N:11]([C:15](=[O:17])[CH3:16])[C:12](=[O:14])[CH3:13])[N:10]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 12469743dimethyl N-(4-aminobenzoyl)-L-glutamateHCID 135577947HCID 135577947, compound

Product 1

HCID 135577948HCID 135577948, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)acetaldehyde (1.74 g, 5.92 mmol) and dimethyl N-(4-aminobenzoyl)-L-glutamate (J. Am. Chem. Soc., 1958, 80, 5779) (1.74 g, 5.92 mmol) in acetic acid (90 ml) was stirred for 10 minutes. Sodium cyanoborohydride (0.84 g, 13.4 mmol) was added in small portions over 1 hour. After an additional 30 minutes, the reaction was spin evaporated in vacuo to a thick oil. The oil was dissolved in ethyl acetate (500 ml) and washed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml), dried with magnesium sulfate and spin evaporated in vacuo. Recrystallization from ethyl acetate, with filtration to remove insolubles, yielded 1.5 g (49% of theory) of dimethyl N-[4-[2-(2-acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)ethylamino]benzoyl]-L-glutamate, mp 168°-178° C. Recrystallization from ethyl acetate (Norite) gave 0.830 g (25% of theory) of the analytical sample, mp 176°-179° C.

Workup

  1. customevaporated in vacuo to a thick oil
  2. dissolutionThe oil was dissolved in ethyl acetate (500 ml)
  3. washwashed with 5% aqueous sodium bicarbonate until neutral, water (50 ml), brine (50 ml)
  4. dry with materialdried with magnesium sulfate
  5. customspin evaporated in vacuo
  6. customRecrystallization from ethyl acetate
  7. filtrationwith filtration
  8. customto remove insolubles

Sources & evidence

ORD record
ord-8d5214c7d00a4bfc9dcd2383595b1050
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04940713

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes