Fmoc-L-Tyr(tBu)-OH → HCID 67448230, compound

HRID 2361997Notes

Reaction equation

HRID 2361997 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][NH:5][CH2:6][CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[CH:19]1[C:31]2[CH:30]([CH2:32][O:33][C:34]([NH:36][C@@H:37]([CH2:41][C:42]3[CH:47]=[CH:46][C:45]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:44][CH:43]=3)[C:38](O)=[O:39])=[O:35])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1>>[C:49]([O:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][C@H:37]([NH:36][C:34](=[O:35])[O:33][CH2:32][CH:30]2[C:31]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]3[C:29]2=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:38]([N:5]([CH2:6][CH:7]([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:4][C:3]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:2]=2[F:1])=[O:39])=[CH:47][CH:46]=1)([CH3:52])([CH3:50])[CH3:51]

Participants

3

Reactant 2

HCID 10895791Fmoc-L-Tyr(tBu)-OHHCID 66978200HCID 66978200, compound

Product 1

HCID 67448230HCID 67448230, compoundYield 36.8%

Procedure

According to the procedure described in the synthesis method of Compound III-1 with the modification that the reaction was carried out overnight, N-(2,4-difluorobenzyl)-2,2-diethoxyethanamine (Compound IX-17) (49.3 g, 190 mmol) was coupled with (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-tert-butoxyphenyl)propanoic acid (128.6 g, 280 mmol) and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1) to obtain the title compound (49.0 g, 36%).

Workup

  1. customdescribed in the synthesis method of Compound III-1 with the modification that the reaction
  2. customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-76762823fbfa46709426e2be2a3094c1
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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