Hydrochloric Acid → HCID 86750112, compound

HRID 1082169Notes

Reaction equation

HRID 1082169 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-a2684c8d80b446028937b3cda7d7bc45
Source dataset
uspto-grants-1996_12
Patent number
US05589473

Reaction notes

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