Penicillin G → HCID 11100316, compound

HRID 653857Notes

Reaction equation

FC(F)(F)C([O-])=O.C1(CC([NH:17][C@@H:18]2[C:39](=[O:40])[N:20]3[C:21]([C:36]([OH:38])=[O:37])=[C:22](/[CH:25]=[CH:26]/[CH2:27][N+:28]([CH2:32][C:33](=[O:35])[NH2:34])([CH2:30][CH3:31])[CH3:29])[CH2:23][S:24][C@H:19]23)=O)C=CC=CC=1.CC1(C)S[C@@H]2[C@H](NC(CC3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O>>[NH2:17][C@@H:18]1[C:39](=[O:40])[N:20]2[C:21]([C:36]([O-:38])=[O:37])=[C:22](/[CH:25]=[CH:26]/[CH2:27][N+:28]([CH2:32][C:33](=[O:35])[NH2:34])([CH2:30][CH3:31])[CH3:29])[CH2:23][S:24][C@H:19]12

Participants

Reactant 2

HCID 5904Penicillin G

HCID 131717449HCID 131717449, compound

Product 1

HCID 11100316HCID 11100316, compoundYield 23.8%

Procedure

In a similar manner as in Example 6 except for the use of paratoluenesulfonic acid monohydrate in place of perchloric acid, the compound (5.9 g) of Example 12 was hydrolyzed using "Carrier-Fixed Penicillin G Amidase" (5.9 g) to obtain the target product (0.85 g).

Sources & evidence

ORD record: ord-6e573b5d12d3433f84617747ff1a2dec
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05128465

Reaction notes

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