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

HRID 2274669Notes

Reaction equation

HRID 2274669 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH2:11][NH:12][C@@H:13]([CH3:21])[CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[CH:9][S:10][C:5]2=[CH:4][CH:3]=1.[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37]([NH:39][C@@H:40]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:47][CH:46]=3)[C:41](O)=[O:42])=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1>>[C:52]([O:51][C:48]1[CH:47]=[CH:46][C:45]([CH2:44][C@H:40]([NH:39][C:37](=[O:38])[O:36][CH2:35][CH:33]2[C:34]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:27]3[C:32]2=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:41]([N:12]([CH2:11][C:8]2[C:6]3=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=[C:5]3[S:10][CH:9]=2)[C@@H:13]([CH3:21])[CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])=[O:42])=[CH:50][CH:49]=1)([CH3:55])([CH3:53])[CH3:54]

Participants

3

Reactant 2

HCID 10895791Fmoc-L-Tyr(tBu)-OHHCID 86652569(S)-N-((5-chlorothieno[3,2-b]pyridin-3-yl)methyl)-1,1-diethoxypropan-2-amine

Product 1

HCID 86698529(9H-fluoren-9-yl)methyl (S)-3-(4-tert-butoxyphenyl)-1-(((5-chlorothieno[3,2-b]pyridin-3-yl)methyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamateYield 55.3%

Procedure

According to the procedure described in the synthesis method of Compound III-5, (S)—N-((5-chlorothieno[3,2-b]pyridin-3-yl)methyl)-1,1-diethoxypropan-2-amine (Compound IX-11) (996 mg, 3.03 mmol) was coupled with (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid (1.53 g, 3.33 mmol) and the obtained residue was purified by Büch silica gel column chromatography (eluent: chloroform:methanol=98:2) to obtain the title compound (1.29 g, 55%).

Workup

  1. customthe obtained residue was purified by Büch silica gel column chromatography (eluent: chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-e147bf0b34c049bc8ddd348c82674c76
Source dataset
uspto-grants-2015_09
Patent number
US09126981B2

Reaction notes

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