Fmoc-L-Tyr(tBu)-OH → (9H-fluoren-9-yl)methyl(S)-1-((benzo[c][1,2,5]thiadiazol-4-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate

HRID 2361988Notes

Reaction equation

HRID 2361988 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([CH2:10][NH:11][C@@H:12]([CH3:20])[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:21]1[C:33]2[CH:32]([CH2:34][O:35][C:36]([NH:38][C@@H:39]([CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:46][CH:45]=3)[C:40](O)=[O:41])=[O:37])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]=2[CH:24]=[CH:23][CH:22]=1>>[N:1]1[S:2][N:3]=[C:4]2[C:9]([CH2:10][N:11]([C@@H:12]([CH3:20])[CH:13]([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])[C:40](=[O:41])[C@@H:39]([NH:38][C:36](=[O:37])[O:35][CH2:34][CH:32]3[C:33]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]4[C:31]3=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:46][CH:45]=3)=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 2

HCID 10895791Fmoc-L-Tyr(tBu)-OHHCID 67088326(S)-N-(benzo[c][1,2,5]thiadiazol-4-ylmethyl)-1,1-diethoxypropan-2-amine

Product 1

HCID 86698532(9H-fluoren-9-yl)methyl(S)-1-((benzo[c][1,2,5]thiadiazol-4-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-3-(4-tert-butoxyphenyl)-1-oxopropan-2-ylcarbamate

Procedure

According to the procedure described in the synthesis method of Compound III-5, (S)—N-(benzo[c][1,2,5]thiadiazol-4-ylmethyl)-1,1-diethoxypropan-2-amine (Compound IX-8) (1.41 g, 4.78 mmol) was coupled with (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid (2.4 g, 5.23 mmol) and the obtained residue was purified by Büch silica gel column chromatography (eluent: n-hexane:ethyl acetate=7:3) to obtain the title compound (2.38% g, 68%).

Workup

  1. customthe obtained residue was purified by Büch silica gel column chromatography (eluent: n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-ad12ddd6ad7a48e8b3dd409282ca41e7
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

Loading…