Diphenylacetic Acid → (R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

HRID 366075Notes

Reaction equation

HRID 366075 reaction equation
Cl.[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH3:22])=[O:19])[NH2:17])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:30]1([CH:36]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:37](O)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C>[C:2]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@@H:21]([C:23]1[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=1)[CH3:22])=[O:19])[NH:17][C:37](=[O:38])[CH:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:3]

Participants

6

Reactant 4

HCID 8333Diphenylacetic AcidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86755918(R)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride

Product 1

HCID 131722082(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amideYield 19.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the method described in Example 3(c) above from (R)-N5 -(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride (3.3 g; 7.8 mmol; from step (b) above), diphenylacetic acid (1.82 g, 8.6 mmol), BOP (3.79 g; 8.58 mmol) and triethylamine (4.0 mL; 1.1 eq.) in 300 mL acetonitrile, yielding 895 mg of the sub-title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-773a1a10ecd34f648fceea6f6428cff4
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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