HCID 178482952, compound → HCID 178482951, compound

HRID 547266Notes

Reaction equation

HRID 547266 reaction equation
[C:1]([C:4]1[C:21](=[O:22])[C@:20]2([OH:23])[C@@H:7]([CH2:8][C@H:9]3[C:18](=[C:19]2[OH:24])[C:17](=[O:25])[C:16]2[C:15]([OH:26])=[C:14]([NH:27][C:28]([C@@H:30]4[CH2:34][CH2:33][CH2:32][N:31]4C(OCC4C=CC=CC=4)=O)=[O:29])[CH:13]=[C:12]([N:45]([CH3:47])[CH3:46])[C:11]=2[CH2:10]3)[C@H:6]([N:48]([CH3:50])[CH3:49])[C:5]=1[OH:51])(=[O:3])[NH2:2]>CO.[Pd]>[C:1]([C:4]1[C:21](=[O:22])[C@:20]2([OH:23])[C@@H:7]([CH2:8][C@H:9]3[C:18](=[C:19]2[OH:24])[C:17](=[O:25])[C:16]2[C:15]([OH:26])=[C:14]([NH:27][C:28]([C@@H:30]4[CH2:34][CH2:33][CH2:32][NH:31]4)=[O:29])[CH:13]=[C:12]([N:45]([CH3:46])[CH3:47])[C:11]=2[CH2:10]3)[C@H:6]([N:48]([CH3:50])[CH3:49])[C:5]=1[OH:51])(=[O:3])[NH2:2]

Participants

4

Reactant 1

HCID 178482952HCID 178482952, compound

Product 1

HCID 178482951HCID 178482951, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of (S)-benzyl 2-((5aR,6aS,7S,10aS)-9-carbamoyl-4,7-bis(dimethylamino)-1,8,10a,11-tetrahydroxy-10,12-dioxo-5,5a,6,6a,7,10,10a,12-octahydrotetracen-2-ylcarbamoyl)pyrrolidine-1-carboxylate (200 mg, 0.29 mmol) and 10% Pd on charcoal in methanol (10 mL) was hydrogenated over 1 h. The reaction mixture was filtered through a pad of celite and the filtrate was poured into ether containing HCl to get (S)—N-((5aR,6aS,7S,10aS)-9-carbamoyl-4,7-bis(dimethylamino)-1,8,10a,11-tetrahydroxy-10,12-dioxo-5,5a,6,6a,7,10,10a,12-octahydrotetracen-2-yl)pyrrolidine-2-carboxamide (120 mg, 72%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. additionthe filtrate was poured into ether
  3. additioncontaining HCl

Sources & evidence

ORD record
ord-4156162a1f7f4acbb8de6efab0b2d910
Source dataset
uspto-grants-2011_05
Patent number
US07939513B2

Reaction notes

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