Formaldehyde → HCID 19972731, compound

HRID 1452337Notes

Reaction equation

N[C:2]1[CH:3]=[C:4]([C:20](=[O:39])[NH:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[CH2:27][CH2:26]2)[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]([CH3:17])[C:7](=[O:18])[C:6]=2[CH:19]=1.[CH2:40]=O.[C:42]([BH3-])#[N:43].[Na+]>>[CH3:40][N:43]([CH3:42])[C:2]1[CH:3]=[C:4]([C:20](=[O:39])[NH:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH3:38])[CH2:27][CH2:26]2)[C:5]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]([CH3:17])[C:7](=[O:18])[C:6]=2[CH:19]=1

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 19972446HCID 19972446, compound

Product 1

HCID 19972731HCID 19972731, compound

Procedure

The title compound was prepared according to Example 35, but using the compound prepared in Example 94 instead of that prepared in Example 33, reacting 10 molar equivalents of 40% formaldehyde instead of 7 molar equivalents and 3 moles of sodium cyanoborohydride instead of 2 moles and stirring at room temperature for 18 hours instead of 4.5 hours. After the usual workup, the crude was purified by column chromatography on silica gel eluting with chloroform-methanol 97:3. Evaporation in vacuo of the collected fractions and crystallization of the residue from ethanol yielded the title compound which melted at 183°-186° C.

Workup

customThe title compound was prepared
customthat prepared in Example 33
customAfter the usual workup, the crude was purified by column chromatography on silica gel eluting with chloroform-methanol 97:3
customEvaporation
customin vacuo of the collected fractions and crystallization of the residue from ethanol

Sources & evidence

ORD record: ord-6a2b6c15675f45cc88e315a7a5560804
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05605896

Reaction notes

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