Acetic Anhydride → HCID 432743, compound

HRID 1904055Notes

Reaction equation

HRID 1904055 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([O:8][CH:9]2[C:14]3[C:15]([OH:42])=[C:16]4[C:27](=[O:28])[C:26]5[C:21](=[C:22]6[O:35][CH:34]7[O:36][C:30]([CH3:41])([CH:31]([OH:40])[CH:32]([NH:38][CH3:39])[CH:33]7[OH:37])[C:23]6=[CH:24][C:25]=5[OH:29])[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[CH:12]([C:43]([O:45][CH3:46])=[O:44])[C:11]([OH:48])([CH3:47])[CH2:10]2)[CH:5]([O:49][CH3:50])[C:4]([O:52][CH3:53])([CH3:51])[CH:3]1[O:54][CH3:55].[C:56](OC(=O)C)(=[O:58])[CH3:57]>CO>[CH3:1][CH:2]1[O:7][CH:6]([O:8][CH:9]2[C:14]3[C:15]([OH:42])=[C:16]4[C:27](=[O:28])[C:26]5[C:21](=[C:22]6[O:35][CH:34]7[O:36][C:30]([CH3:41])([CH:31]([OH:40])[CH:32]([N:38]([C:56]([CH3:57])=[O:58])[CH3:39])[CH:33]7[OH:37])[C:23]6=[CH:24][C:25]=5[OH:29])[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[CH:12]([C:43]([O:45][CH3:46])=[O:44])[C:11]([OH:48])([CH3:47])[CH2:10]2)[CH:5]([O:49][CH3:50])[C:4]([O:52][CH3:53])([CH3:51])[CH:3]1[O:54][CH3:55]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 432741HCID 432741, compound

Product 1

HCID 432743HCID 432743, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Eight hundred mg of N-demethylnogalamycin is dissolved in a mixture of 10 ml of methanol and 2 ml of acetic anhydride. After the solution has stood at room temperature for 4 hours, it is evaporated to dryness under reduced pressure. The residue is chromatographed on 90 g of silica gel using chloroform-methanol (19:1) and collecting 201 five-ml fractions. Fractions 100-201 are combined and evaporated to dryness in vacuo to give 470 mg of N-acetyl-N-demethylnogalamycin; homogenous by TLC, Rf 0.38 in CHCl3 --CH3OH (9:1); [α]D +485°; (c 0.286, CHCl3); UV (EtOH) 236 nm (ε38,400), 258 nm (ε19,200), 290sh nm (ε12,800); IR (Nujol) 3380, 1715, 1705, 1650, 1615, 1585, 1285, 1215, 1135, 1100, 1045, 1025, 1000, 915, 875, 820, 750 cm-1 ; 1H NMR (CDCl3) δ1.1-1.7 (m, 12H), 2.10 (s, 3H), 3.20 (s, 3H), 3.25, 3.53, 3.62, 3.68 (4s, 12H), 2.8-4.62 (m), 5.22, 5.55, 5.88 (3 broad s, 3H), 7.26 (s, 1H), 7.52 (s, 1H), 13C NMR (CDCl3) δ191.1, 179.8, 174.7, 171.6, 161.6, 155.8, 146.9, 143.8, 136.5, 133.5, 130.4, 125.2, 116.1, 114.2, 113.9, 100.7, 95.92, 84.3, 81.0, 77.8, 75.7, 74.0, 71.5, 69.4, 67.3, 61.1, 59.2, 58.7, 56.8, 52.2, 48.5, 40.0, 32.2, 29.4, 23.6, 22.4, 18.0, 14.6; mass spectrum m/e 815.

Workup

  1. customit is evaporated to dryness under reduced pressure
  2. customThe residue is chromatographed on 90 g of silica gel
  3. customcollecting 201 five-ml fractions
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-cda6d9dc7267412cb0fc14bf862ed39f
Source dataset
uspto-grants-1984_03
Patent number
US04439602

Reaction notes

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