Indole → HCID 16204229, compound

HRID 2370462Notes

Reaction equation

HRID 2370462 reaction equation
[NH2:1][C:2]([C:5]([OH:7])=O)([CH3:4])[CH3:3].[NH2:8][C@H:9]([C:20](O)=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1.N1[CH:36]=[CH:35][N:34]=[N:33]1>>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:10][CH2:9][N:8]2[C:35]([CH2:36][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:34][N:33]=[C:20]2[C@H:9]([NH:8][C:5](=[O:7])[C:2]([NH2:1])([CH3:4])[CH3:3])[CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[CH:24]1

Participants

5

Reactant 4

HCID 798Indole8×HCID 6119Aminoisobutyric acidHCID 6305L-Tryptophan7×HCID 178418936HCID 178418936, compound2×

Product 1

HCID 16204229HCID 16204229, compound

Procedure

δ (ppm) 23.5 (CH3 Aib), 23.7 (CH3 Aib), 29.6 (CH2 βTrp), 30.3 (CH2-benzyl and CH2—CH2-indole), 44.1 (CH2—CH2-indole), 46.1 (CH αTrp), 56.8 (Cq Aib), 109.8 (C3 Trp), 109.9 (C3 indole), 111.9 (C7 indole and C7 Trp), 118.3 (C4 Trp), 118.4 (C4 indole), 118.9 (C5 indole and C5 Trp), 121.3 (C6 Trp), 121.5 (C6 indole), 123.7 (C2 indole), 124.7 (O2 Trp), 127.0 (C9 indole), 127.2 (C2 and C6 benzyl), 127.4 (C9 Trp), 128.8 (C3 and C5 benzyl), 129.0 (C4 benzyl), 136.3 (C1 benzyl), 136.4 (C8 indole and C8 Trp), 153.1 (Cq triazole), 155.3 (Cq triazole), 171.8 (CO Aib).

Sources & evidence

ORD record
ord-394195fb85c5498c93aca09dd2049ab4
Source dataset
uspto-grants-2014_04
Patent number
US08710089B2

Reaction notes

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