Triethylamine → (+)-5-Methoxycarbonyl-4-methyoxymethyl-1, 2,3,6-tetrahydro-2-oxo-6(S)-(3,4-difluorophenyl)-1-[(2-ethoxycarbonylethylamino)carbonyl]pyrimidine

HRID 1840324Notes

Reaction equation

HRID 1840324 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].[CH3:10][O:11][C:12]([C:14]1[C@H:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)[N:18]([C:28](OC2C=CC([N+]([O-])=O)=CC=2)=[O:29])[C:17](=[O:40])[NH:16][C:15]=1[CH2:41][O:42][CH3:43])=[O:13].C(N(CC)CC)C>ClCCl>[CH3:10][O:11][C:12]([C:14]1[C@H:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)[N:18]([C:28]([NH:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])=[O:29])[C:17](=[O:40])[NH:16][C:15]=1[CH2:41][O:42][CH3:43])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 155126495-methyl 1-(4-nitrophenyl) (6S)-6-(3,4-difluorophenyl)-4-(methoxymethyl)-2-oxo-3,6-dihydro-1,5(2H)-pyrimidinedicarboxylate

Product 1

HCID 60101878(+)-5-Methoxycarbonyl-4-methyoxymethyl-1, 2,3,6-tetrahydro-2-oxo-6(S)-(3,4-difluorophenyl)-1-[(2-ethoxycarbonylethylamino)carbonyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

β-Alanine ethyl ester hydrochloride (87 mg, 0.57 mmol), (+)-5-methyoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro-2-oxo-6 (S)-(3,4-difluorophenyl)-1-[(4-nitrophenyloxy)-carbonyl]pyrimidine (as described in Section I.A.(c)) (227 mg, 0.48 mmol), and triethylamine (209 mL, 1.50 mmol) were combined in 5 mL of dichloromethane. The yellow mixture was stirred at ambient temperature for 1 hour, then evaporated to dryness. The resulting oil was purified by “flash” chromatography (5.02, 98:2:0.2 of dichloromethane: methanol:ammonium hydroxide). The product fractions were evaporated to dryness to give the title compound as a clear oil.

Workup

  1. customevaporated to dryness
  2. customThe resulting oil was purified by “flash” chromatography (5.02, 98:2:0.2 of dichloromethane: methanol:ammonium hydroxide)
  3. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-31a7db8791c34814aad39bf8fab919c0
Source dataset
uspto-grants-2004_01
Patent number
US06680323B2

Reaction notes

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