Hydrochloric Acid → HCID 86750112, compound

HRID 234231Notes

Reaction equation

HRID 234231 reaction equation
C[Si](C)(C(C)(C)C(C)C)[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][CH2:12][C@H:11]([O:29][C:30](=[O:40])[C@@H:31]([NH:33]C(OCC=C)=O)[CH3:32])[O:10][C:9](=[O:41])[C:8]=2[C:7]([CH3:42])=[C:6]([O:43][CH3:44])[CH:5]=1.[F-].[NH4+].[ClH:54]>CO.C(OCC)(=O)C.C(OCC)C>[ClH:54].[OH:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][CH2:12][C@H:11]([O:29][C:30](=[O:40])[C@@H:31]([NH2:33])[CH3:32])[O:10][C:9](=[O:41])[C:8]=2[C:7]([CH3:42])=[C:6]([O:43][CH3:44])[CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 25516Ammonium fluorideHCID 53656144HCID 53656144, compound

Product 1

HCID 86750112HCID 86750112, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-Allyloxycarbonylamino-propionic acid (4R,10S)-16-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-12-oxo-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-10-yl ester was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 1. The resulting product was dissolved in ethyl acetate. Upon addition of 3N hydrochloric acid in diethyl ether, a precipitate formed which was collected to yield (S)-2-amino-propionic acid (4R,10S)-16-hydroxy-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-12-oxo-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-10-yl ester hydrochloride as a white solid.

Workup

  1. customa precipitate formed which
  2. customwas collected

Sources & evidence

ORD record
ord-13fb25064ba24e8fb6411c40c4eb5c8a
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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