3,5-Dimethylbenzoyl Chloride → HCID 67674610, compound

HRID 1956972Notes

Reaction equation

HRID 1956972 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[C:5]([N:7]([CH:19]([CH3:22])[CH2:20][CH3:21])[C@@H:8]([C:16](O)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6].COC(=O)[C@@H](CC1C=CC=CC=1)N.C([BH3-])#N.[Na+].CC1C=C(C=C(C)C=1)C(Cl)=O.Cl.C[O:57][C:58](=[O:71])[C@H:59]([CH2:61][C:62]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[NH:64][CH:63]=1)[NH2:60]>CN(C1C=CN=CC=1)C.C(C(C)=O)C>[CH3:26][C:24]1[CH:23]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:25]=1)[C:5]([N:7]([CH:19]([CH3:22])[CH2:20][CH3:21])[C@@H:8]([C:16]([NH:60][C@H:59]([C:58]([OH:57])=[O:71])[CH2:61][C:62]1[C:70]2[C:65](=[CH:66][CH:67]=[CH:68][CH:69]=2)[NH:64][CH:63]=1)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6]

Participants

8

Reactant 5

HCID 810883,5-Dimethylbenzoyl ChlorideHCID 853474(R)-Methyl 2-amino-3-phenylpropanoateHCID 2734891Methyl tryptophanate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 67674858HCID 67674858, compound

Product 1

HCID 67674610HCID 67674610, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Following the procedure described in example 12 and starting from N-(3,5-dimethylbenzoyl)-N-(1-methylpropyl)-(D)-phenylalanine (prepared by reductive alkylation of (D)-phenylalanine methyl ester with ethylmethylketone in the presence of sodium cyanoborohydride followed by N-acylation with 3,5-dimethylbenzoyl chloride in the presence of DMAP and hydrolysis of the methyl ester moiety according to example 1 and (L)-tryptophan methyl ester hydrochloride gives N-(3,5-dimethylbenzoyl)-N-(1-methylpropyl)-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 540 (M+H)+.

Sources & evidence

ORD record
ord-aaa0873cb9c247ae9d3a23fd5d2daa2c
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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