Cyclohexanone → HCID 67675208, compound

HRID 1956975Notes

Reaction equation

HRID 1956975 reaction equation
C[C:2]1[CH:3]=[C:4]([CH:25]=[C:26](C)[CH:27]=1)C(N(C1CCCCC1)[C@@H](C(O)=O)CC1C=CC=CC=1)=O.CO[C:31](=[O:41])[C@@H:32]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH2:33].C1(=O)CCCCC1.C([BH3-])#N.[Na+].[CH3:53][C:54]1[CH:55]=[C:56]([CH:60]=[C:61]([CH3:63])[CH:62]=1)[C:57](Cl)=[O:58].Cl.C[O:66][C:67](=[O:80])[C@H:68]([CH2:70][C:71]1[C:79]2[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=2)[NH:73][CH:72]=1)[NH2:69]>CN(C1C=CN=CC=1)C>[CH3:53][C:54]1[CH:55]=[C:56]([CH:60]=[C:61]([CH3:63])[CH:62]=1)[C:57]([N:33]([CH:2]1[CH2:3][CH2:4][CH2:25][CH2:26][CH2:27]1)[C@@H:32]([C:31]([NH:69][C@H:68]([C:67]([OH:66])=[O:80])[CH2:70][C:71]1[C:79]2[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=2)[NH:73][CH:72]=1)=[O:41])[CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:58]

Participants

8

Reactant 6

HCID 7967CyclohexanoneHCID 810883,5-Dimethylbenzoyl ChlorideHCID 853474(R)-Methyl 2-amino-3-phenylpropanoateHCID 2734891Methyl tryptophanate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 67674640HCID 67674640, compound

Product 1

HCID 67675208HCID 67675208, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Following the procedure described in example 12 and starting from N-(3,5-dimethylbenzoyl)-N-cyclohexyl-(D)-phenylalanine (prepared by reductive alkylation of (D)-phenylalanine methyl ester with cyclohexanone 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-cyclohexyl-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 566 (M+H)+.

Sources & evidence

ORD record
ord-2f983c89e7664973a15127babe444842
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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