Hydrochloric Acid → HCID 86758173, compound

HRID 2186424Notes

Reaction equation

HRID 2186424 reaction equation
CO.Cl.C(O[C@H]1[C@H](C)O[C@@H]([O:15][C@@H:16]2[C@@H:32]([CH3:33])[C:31](=[O:34])[O:30][C@H:29]([CH2:35][CH3:36])[C@:28]3([CH3:37])[C@H:24]([N:25]([NH:39][CH2:40][CH2:41][C@H:42]([N:44]4[CH:48]=[C:47]([C:49]5[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=5)[N:46]=[CH:45]4)[CH3:43])[C:26](=[O:38])[O:27]3)[C@@H:23]([CH3:55])[C:22](=[O:56])[C@H:21]([CH3:57])[CH2:20][C@:19]([O:59][CH3:60])([CH3:58])[C@H:18]([O:61][C@@H:62]3[O:71][C@H:70]([CH3:72])[CH2:69][C@H:68]([N:73]([CH3:75])[CH3:74])[C@H:63]3[O:64][C:65](=[O:67])[CH3:66])[C@H:17]2[CH3:76])C[C@@]1(C)OC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.CCOC(C)=O>[C:65]([O:64][C@@H:63]1[C@@H:68]([N:73]([CH3:75])[CH3:74])[CH2:69][C@@H:70]([CH3:72])[O:71][C@H:62]1[O:61][C@@H:18]1[C@@H:17]([CH3:76])[C@H:16]([OH:15])[C@@H:32]([CH3:33])[C:31](=[O:34])[O:30][C@H:29]([CH2:35][CH3:36])[C@:28]2([CH3:37])[C@H:24]([N:25]([NH:39][CH2:40][CH2:41][C@H:42]([N:44]3[CH:48]=[C:47]([C:49]4[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=4)[N:46]=[CH:45]3)[CH3:43])[C:26](=[O:38])[O:27]2)[C@@H:23]([CH3:55])[C:22](=[O:56])[C@H:21]([CH3:57])[CH2:20][C@:19]1([O:59][CH3:60])[CH3:58])(=[O:67])[CH3:66]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 86758174HCID 86758174, compound

Product 1

HCID 86758173HCID 86758173, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a reactor is charged methanol and 12N HCl (5 mol). The temperature is set at 30° C. and (3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-8-[[4-O-Acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl]oxy]-4-ethyldecahydro-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[[(3R)-3-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]amino]-10-[[2-O-acetyl-3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-2H-Oxacyclotetradecino[4,3-d]oxazole-2,6,14(1H,7H)-trione (17) (1 mol) is added. The reaction is stirred to dissolve the solids, then it is heated to 45° C. until complete. Once the reaction is complete, the methanol is removed in vacuo, and the internal temperature is set at 20° C. The reaction is extracted between sodium carbonate (6 mol) in water and EtOAc. The aqueous layer is separated, and the organic layer is concentrated to low volume. The product (19) is then isolated.

Workup

  1. customis set at 30° C.
  2. dissolutionto dissolve the solids
  3. customthe methanol is removed in vacuo
  4. customis set at 20° C
  5. customThe aqueous layer is separated
  6. concentrationthe organic layer is concentrated to low volume

Sources & evidence

ORD record
ord-45b5ac0fcd794d7cb8ddb80091911302
Source dataset
uspto-grants-2002_06
Patent number
US06403776B1

Reaction notes

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