Hydrochloric Acid → HCID 86750112, compound

HRID 1377865Notes

Reaction equation

HRID 1377865 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-d9749440346c405c9cb7a59d4adaa4cf
Source dataset
uspto-grants-1997_09
Patent number
US05665746

Reaction notes

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