HCID 6993434, compound → HCID 5276157, compound

HRID 1788409Notes

Reaction equation

HRID 1788409 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16](O)=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=[CH:22]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:35][C@H:36]([C:49]([O:51]C(C)(C)C)=[O:50])[CH2:37][CH2:38][CH2:39][CH2:40][NH:41]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[NH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH:36]([NH:35][C:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]=[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:23]=[CH:22]4)=[N:9][C:10]=2[CH:15]=1)=[O:17])[C:49]([OH:51])=[O:50]

Participants

4

Reactant 3

HCID 6993434HCID 6993434, compoundHCID 11213026HCID 11213026, compoundHCID 66633105Anisole trifluoroacetic acid

Product 1

HCID 5276157HCID 5276157, compoundYield 15%

Procedure

Compound 232 was synthesized from Compound 201 as described for Compound 235, except H-Lys(Boc)-OtBu was used instead of L-5-hydroxytryptophane. In the 3rd step the protected intermediate was treated with a mixture of TFA-anisol 8:2 for 2 hours then the product was precipitated with ether and purified on RP-HPLC. Yield 15%.

Workup

  1. customthe product was precipitated with ether
  2. custompurified on RP-HPLC

Sources & evidence

ORD record
ord-35ed362bf35043f095ba059817691909
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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