Ammonia → HCID 14390730, compound

HRID 257543Notes

Reaction equation

HRID 257543 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.C(Cl)Cl.CO.[NH4+].[OH-]>[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

6

Reactant 3

HCID 222AmmoniaHCID 14390733HCID 14390733, compoundHCID 21896990Dichloromethane methanol ammonium hydroxide

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 CH2Cl2 :MeOH:NH4OH (97.5:2.5:0.25) to give the title compound, [α]D26 =-118.2° (MeOH).

Sources & evidence

ORD record
ord-4996b6c9242c4904896ef3b122bae883
Source dataset
uspto-grants-1993_11
Patent number
US05262436

Reaction notes

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