(S)-2-((S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-7-((3R,5S)-1-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-3-phenylpropanoic acid → (S)-1-(5-Methyl-1,3,4-oxadiazol-2-yl)-2-phenylethanamine

HRID 339275Notes

Reaction equation

HRID 339275 reaction equation
C(OC(N(C)[C@@H](C)C(N[C@@H](C(C)(C)C)C(N1[C@H](C(N[C@@H](CC2C=CC=CC=2)C(O)=O)=O)CC2C(=CC([C@H]3C[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)C1)=O)=O)=O)(C)(C)C.[CH3:85][C:86]1[O:90][C:89]([C@@H:91]([NH:99]C(=O)OC(C)(C)C)[CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)=[N:88][N:87]=1>>[CH3:85][C:86]1[O:90][C:89]([C@@H:91]([NH2:99])[CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)=[N:88][N:87]=1

Participants

3

Reactant 2

HCID 86705906(S)-2-((S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-7-((3R,5S)-1-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamido)-3-phenylpropanoic acidHCID 86705919(S)-tert-Butyl (1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl)carbamate

Product 1

HCID 42047875(S)-1-(5-Methyl-1,3,4-oxadiazol-2-yl)-2-phenylethanamineYield 52%

Procedure

Following a procedure analogous to that for the synthesis of Compound B of Example 78, (S)-tert-butyl (1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-phenylethyl)carbamate (130 mg, 0.43 mmol) was converted to the title compound (45 mg, 52% over 2 steps) after preparative HPLC. 1H NMR (CDCl3) δ 7.38-7.14 (m, 1H), 4.43 (dd, J=8.4, 5.5 Hz, 1H), 3.27 (dd, J=13.6, 5.3 Hz, 1H), 3.04 (dd, J=13.6, 8.4 Hz, 1H), 2.53 (s, 3H); MS (ESI+) m/z 204.2 (M+H)+.

Sources & evidence

ORD record
ord-eefecf3fbc394fe4b9f2789bda358655
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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