Ammonia → HCID 14390730, compound

HRID 2292175Notes

Reaction equation

HRID 2292175 reaction equation
C([S:4][CH2:5][CH:6]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH3:11])=[O:8])(=O)C.N>[Zn].CO>[CH2:22]([CH:6]([CH2:5][SH:4])[C:7]([NH:9][C@H:10]([C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])[CH3:11])=[O:8])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 14390733HCID 14390733, compound

Product 1

HCID 14390730HCID 14390730, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent2×

Procedure

Treat the product from Step 1 with methanol saturated with ammonia as described in Example 12, Step 3 (before chromatography). Treat the resultant residue with zinc powder as described in Example 17. Chromatograph the product on flash grade silica gel using CH2Cl2MeOH:NH40H (97.5:2.5:0.25) to give the title compound, [α]D26 =-118.2° (MeOH).

Sources & evidence

ORD record
ord-dcb27c4c08234557b965a5d9df9c7f48
Source dataset
uspto-grants-1989_01
Patent number
US04801609

Reaction notes

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