Carbamate → HCID 67052638, compound

HRID 2276973Notes

Reaction equation

HRID 2276973 reaction equation
[CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([N:15]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])N>CCOC(C)=O.[Pd]>[CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH2:23])[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 276CarbamateHCID 67052653HCID 67052653, compound

Product 1

HCID 67052638HCID 67052638, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of stage 2 carbamate (4.44 g, 9.78 mmol) and 10% Pd/C (0.7 g) in EtOAc (130 ml) was hydrogenated at room temperature for 18 h under balloon pressure. The Pd/C catalyst was filtered off through a pad of celite. The filtrate was concentrated under reduced pressure to yield a white solid (4.25 g). LCMS purity 100%, m/z 425 [M++H]+,

Workup

  1. filtrationThe Pd/C catalyst was filtered off through a pad of celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-02af6a52d476499a9ed93c2b5c070fe8
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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