Cyclohexanecarboxaldehyde → HCID 67676296, compound

HRID 1956974Notes

Reaction equation

HRID 1956974 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[C:28]([CH3:30])[CH:29]=1)[C:5](N(CCC1CCCCC1)[C@@H](C(O)=O)CC1C=CC=CC=1)=[O:6].CO[C:33](=[O:43])[C@@H:34]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH2:35].[CH:44]1([CH:50]=O)[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1.C([BH3-])#N.[Na+].CC1C=C(C=C(C)C=1)C(Cl)=O.Cl.C[O:69][C:70](=[O:83])[C@H:71]([CH2:73][C:74]1[C:82]2[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=2)[NH:76][CH:75]=1)[NH2:72]>CN(C1C=CN=CC=1)C>[CH3:30][C:28]1[CH:27]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:29]=1)[C:5]([N:35]([CH2:50][CH:44]1[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1)[C@@H:34]([C:33]([NH:72][C@H:71]([C:70]([OH:83])=[O:69])[CH2:73][C:74]1[C:82]2[C:77](=[CH:78][CH:79]=[CH:80][CH:81]=2)[NH:76][CH:75]=1)=[O:43])[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:6]

Participants

8

Reactant 6

HCID 16275CyclohexanecarboxaldehydeHCID 810883,5-Dimethylbenzoyl ChlorideHCID 853474(R)-Methyl 2-amino-3-phenylpropanoateHCID 2734891Methyl tryptophanate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 67674649HCID 67674649, compound

Product 1

HCID 67676296HCID 67676296, 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-(cyclohexylethyl)-(D)-phenylalanine (prepared by reductive alkylation of (D)-phenylalanine methyl ester with cyclohexanecarboxaldehyde 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-(cyclohexylmethyl)-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 580 (M+H)+.

Sources & evidence

ORD record
ord-63c27b4791314b08a2c6e2ded2e9b2bc
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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