Acetic Acid → 3-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxypentopyranoside--hydrogen chloride (1/1)

HRID 842584Notes

Reaction equation

HRID 842584 reaction equation
[ClH:1].C(O)(=O)C.[CH3:6][C:7]([C@@:9]1([NH2:40])[CH2:30][C@H:29]([O:31][C@@H:32]2[O:37][CH2:36][C@@H:35]([OH:38])[C@@H:34]([OH:39])[CH2:33]2)[C:12]2[C:13]([OH:28])=[C:14]3[C:26](=[O:27])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:18](=[O:19])[C:15]3=[C:16]([OH:17])[C:11]=2[CH2:10]1)=[O:8].CC(C)=O>O>[CH3:6][C:7]([C@@:9]1([NH2:40])[CH2:30][C@H:29]([O:31][C@@H:32]2[O:37][CH2:36][C@@H:35]([OH:38])[C@@H:34]([OH:39])[CH2:33]2)[C:12]2[C:13]([OH:28])=[C:14]3[C:26](=[O:27])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:18](=[O:19])[C:15]3=[C:16]([OH:17])[C:11]=2[CH2:10]1)=[O:8].[ClH:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180Acetone2×HCID 313Hydrochloric AcidHCID 3035016110267-81-7

Product 1

HCID 1148973-Acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxypentopyranoside--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1N Hydrochloric acid (2.05 g) and acetic acid (0.75 g) were added to a solution of amrubicin (1.0 g) in water (10 g) and acetone (6.7 g) at 0 to 5° C., to adjust the pH to 2.5, and stirred for 30 minutes. The reaction mixture was poured into acetone (280 g) at 30 to 34° C., and stirred for 3 hours. The precipitated crystals were collected by filtration, and washed with acetone (9.8 g) to give wet crystals of amrubicin hydrochloride. The wet crystals were added again to mixture of acetone (280 g) and water (11.8 g), and stirred at 30 to 34° C. for 1 hour. The crystals were collected by filtration, and washed with acetone (9.8 g), and dried under reduced pressure at room temperature.

Workup

  1. stirringstirred for 3 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with acetone (9.8 g)

Sources & evidence

ORD record
ord-73f69293d9c644b2b58d41baf56e2a51
Source dataset
uspto-grants-2002_04
Patent number
US06376469B1

Reaction notes

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