Iodoethane → HCID 67675744, compound

HRID 1956973Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:5]([N:7]([CH2:19][CH3:20])[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)NC(=O)C1C=C(C)C=C(C)C=1.C(I)C.[H-].[Na+].Cl.C[O:55][C:56](=[O:69])[C@H:57]([CH2:59][C:60]1[C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[NH:62][CH:61]=1)[NH2:58]>>[CH3:24][C:22]1[CH:21]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:23]=1)[C:5]([N:7]([CH2:19][CH3:20])[C@@H:8]([C:16]([NH:58][C@H:57]([C:56]([OH:55])=[O:69])[CH2:59][C:60]1[C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[NH:62][CH:61]=1)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6]

Participants

Reactant 5

HCID 6340Iodoethane

HCID 24758Sodium hydride

HCID 2734891Methyl tryptophanate hydrochloride

HCID 67674831HCID 67674831, compound

HCID 67676287HCID 67676287, compound

Product 1

HCID 67675744HCID 67675744, compound

Procedure

Following the procedure described in example 12 and starting from N-(3,5-dimethylbenzoyl)-N-ethyl-(D)-phenylalanine (prepared by alkylation of N-(3,5-dimethylbenzoyl)-(D)-phenylalanine methyl ester with ethyl iodide in the presence of sodium hydride followed by hydrolysis of the methyl ester moiety according to example 1 and (L)-tryptophan methyl ester hydrochloride gives N-(3,5-dimethylbenzoyl)-N-ethyl-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 510 (M-H)-.

Sources & evidence

ORD record: ord-d150c6e1291f4268a2ab292cc9ef9ff3
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780498

Reaction notes

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