Acetic Acid → HCID 131722031, compound

HRID 366032Notes

Reaction equation

HRID 366032 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([NH:34][C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[CH3:36])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OCC1C=CC=CC=1)=O.[CH3:44][C:45]([OH:47])=[O:46]>[Pd]>[C:45]([OH:47])(=[O:46])[CH3:44].[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([NH:16][C@@H:15]([C:32]([NH:34][C@@H:35]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[CH3:36])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86755897HCID 86755897, compound

Product 1

HCID 131722031HCID 131722031, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared analogously to the method described in Example 1(e) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(R)-N-[1-(4-hydroxyphenyl)ethyl]-ornithine amide (26.8 g; 46.23 mmol; from step (d) above), 10% Pd/C (2.5 g) and HOAc (1L; as opposed to HCl/MeOH) yielding 24.3 g of the sub-title compound (after azeotroping with toluene).

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-7abf19b92ef34b2f9444492deabf0d86
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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