(S)-1-tert-Butyl 2-methyl 4-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrrole-1,2(2H,5H)-dicarboxylate → (S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

HRID 339281Notes

Reaction equation

C(OC(N(C)[C@@H](C)C(N[C@@H](C(C)(C)C)C(N1C[C@@H](C2C=C3C(C[C@@H](C(=O)N[C@H]4C5C(=CC=CC=5)CCC4)N(C(=O)[C@@H](NC(=O)[C@@H](N(C(OC(C)(C)C)=O)C)C)C(C)(C)C)C3)=CC=2)C[C@H]1C(N[C@@H](CC1C=CC=CC=1)C(O)=O)=O)=O)=O)=O)(C)(C)C.FC(F)(F)S(O[C:91]1[CH2:95][N:94]([C:96]([O:98][C:99]([CH3:102])([CH3:101])[CH3:100])=[O:97])[C@H:93]([C:103]([O:105][CH3:106])=[O:104])[CH:92]=1)(=O)=O.CC1(C)C(C)(C)OB([C:117]2[CH:126]=[C:125]3[C:120]([CH2:121][C@@H:122]([C:134]([O:136][CH3:137])=[O:135])[N:123]([C:127]([O:129][C:130]([CH3:133])([CH3:132])[CH3:131])=[O:128])[CH2:124]3)=[CH:119][CH:118]=2)O1>>[C:99]([O:98][C:96]([N:94]1[C@H:93]([C:103]([O:105][CH3:106])=[O:104])[CH:92]=[C:91]([C:117]2[CH:126]=[C:125]3[C:120]([CH2:121][C@@H:122]([C:134]([O:136][CH3:137])=[O:135])[N:123]([C:127]([O:129][C:130]([CH3:131])([CH3:132])[CH3:133])=[O:128])[CH2:124]3)=[CH:119][CH:118]=2)[CH2:95]1)=[O:97])([CH3:102])([CH3:101])[CH3:100]

Participants

Reactant 3

HCID 11773246(S)-1-tert-Butyl 2-methyl 4-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrrole-1,2(2H,5H)-dicarboxylate

HCID 86705903(S)-2-tert-butyl 3-methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

HCID 86705917(S)-2-((2S,4R)-1-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-4-((S)-2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)pyrrolidine-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 86705924(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylateYield 70%

Procedure

Following a procedure analogous to that for the synthesis of Compound D of Example 22, (S)-1-tert-butyl 2-methyl 4-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrrole-1,2(2H,5H)-dicarboxylate (585 mg, 1.56 mmol) and (S)-2-tert-butyl 3-methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (650 mg, 1.56 mmol) were converted to the title compound (563 mg, 70%). MS (ESI+) m/z 517.4 (M+H)+.

Sources & evidence

ORD record: ord-2e7c1342f20e4788938eae00e16b665a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

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