Rifamycin S → Rifamycin

HRID 1388495

Reaction equation

HRID 1388495 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27]([NH:29][C:30]4[C:34](=[O:35])[C:4](=[C:5]([C:32](=[O:33])[CH:31]=4)[C:6]=2[C:10]3=[O:11])[C:3]=1[OH:50])=[O:28]>CC1C2OC3(C)C(C=2C2C(OCC(NC4C=CC(I)=CC=4)=O)=CC(NC(C(C)=CC=CC(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)C=CO3)=O)=C(O)C=2C=1O)=O>[CH3:1][C:2]1[C:7]2[O:8][C@@:9]3([CH3:49])[C:10]([C:6]=2[C:5]2[C:32]([OH:33])=[CH:31][C:30]([NH:29][C:27]([C:26]([CH3:36])=[CH:25][CH:24]=[CH:23][C@H:22]([CH3:37])[C@H:21]([OH:38])[C@@H:20]([CH3:39])[C@@H:19]([OH:40])[C@@H:18]([CH3:41])[C@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:16]([CH3:46])[C@@H:15]([O:47][CH3:48])[CH:14]=[CH:13][O:12]3)=[O:28])=[C:34]([OH:35])[C:4]=2[C:3]=1[OH:50])=[O:11]

Participants

3

Reactant 1

HCID 6436726Rifamycin S

Product 1

HCID 6324616Rifamycin

Reagents, catalysts & solvents 1

HCID 6507126[(9E,19E,21Z)-2,15,17,29-tetrahydroxy-27-[2-(4-iodoanilino)-2-oxoethoxy]-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetateSolvent

Conditions

Temperature
50 °C

Procedure

Reaction--Ten grams of the enzyme adsorbed on celite were added to 300 ml of 1% rifamycin B solution (10 mM phosphate buffer, pH 8.5). The conversion to rifamycin S was completed in 7 hours of reaction at 40° C. with aeration and agitation. The celite filter cake recovered by filtration on a sintered glass was washed with 200 ml of methanol. The final methanolic aqueous solution of rifamycin S was warmed to 50° C. in order to solubilize completely the residual rifamycin S precipitate. 30 ml of 5% ascorbic acid solution in water was added thereto dropwisely while continuous stirring. The purpose color of rifamycin S was gradually changed to the deep red color of rifamycin SV. After adjusting the final pH to 4.0, the methanol was completely evaporated using suction evaporator at 40° C. Afte chilling the final solution at 4° C. for 2 days, the rifamycin SV crystals were recovered by filtration. 2.4 gr of deep yellowish rifamycin SV crystals were obtained after drying over sodium sulfate (yield=87%).

Workup

  1. customReaction
  2. filtrationThe celite filter cake
  3. filtrationrecovered by filtration on a sintered glass
  4. washwas washed with 200 ml of methanol
  5. addition30 ml of 5% ascorbic acid solution in water was added
  6. customthe methanol was completely evaporated
  7. customsuction evaporator at 40° C
  8. temperatureAfte chilling the final solution at 4° C. for 2 days
  9. filtrationthe rifamycin SV crystals were recovered by filtration

Sources & evidence

ORD record
ord-835ab6c1bbac4370bf72cee22524c5c0
Source dataset
uspto-grants-1984_02
Patent number
US04431735

Linked notes

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