Chloromethyl Methyl Ether → 3-benzyloxycarbonylamino-6-methoxymethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid tert-butyl Ester

HRID 10983

Reaktionsgleichung

Reaktionsgleichung von HRID 10983
[C:1]([O:5][C:6]([C:8]1([CH3:29])[N:12]2[C:13](=[O:28])[C:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[CH:15][N:16]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([O:37]C(NC1C(=O)N2[C@H](C(OC(C)(C)C)=O)CCC2=NC=1)=O)C1C=CC=CC=1.COCCl>>[C:1]([O:5][C:6]([C:8]1([CH2:29][O:37][CH3:30])[N:12]2[C:13](=[O:28])[C:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[CH:15][N:16]=[C:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 7864Chloromethyl Methyl EtherHCID 54224046tert-Butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylateHCID 696008793-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid tert-butyl Ester

Produkt 1

HCID 696005813-benzyloxycarbonylamino-6-methoxymethyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid tert-butyl EsterAusbeute 36 %

Versuchsvorschrift

According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with methoxymethylchloride afforded 101 mg (36%) of intermediate 23a. MS (ESI) 430.4 (M+H+), 452.4 (M+Na+).

Quellen und Nachweise

ORD-Eintrag
ord-2fe581f8f38b40a180f0106c06d749ed
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094783B2

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