L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamate

HRID 339278Notes

Reaction equation

HRID 339278 reaction equation
C(OC(N(C)[C@@H](C)C(N[C@@H](C(C)(C)C)C(N1C[C@@H]([C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][C@@H:26]([C:52](=[O:64])[NH:53][C@H:54]4[C:63]5[C:58](=CC=CC=5)CCC4)[N:27]([C:31](=[O:51])[C@@H](NC(=O)[C@@H](N(C(OC(C)(C)C)=O)C)C)C(C)(C)C)C3)=[CH:23][CH:22]=2)C[C@H]1C(N[C@@H](CC1C=CC=CC=1)C(O)=O)=O)=O)=O)=O)(C)(C)C.[C:85]([O:89]C(N[C@@H](CC1C=CC=CC=1)C(O)=O)=O)([CH3:88])([CH3:87])[CH3:86].C(N)C#C>>[O:64]=[C:52]([NH:53][CH2:54][C:63]#[CH:58])[C@@H:26]([NH:27][C:31](=[O:51])[O:89][C:85]([CH3:88])([CH3:87])[CH3:86])[CH2:25][C:24]1[CH:23]=[CH:22][CH:21]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 239041PropargylamineHCID 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 11673861tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamateYield 99%

Procedure

Following a procedure analogous to that for the synthesis of Compound D of Example 1, (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (Aldrich, 355 mg, 1.34 mmol) and prop-2-yn-1-amine (Combi-Blocks, 86 μL, 1.34 mmol) were converted to the title compound (401 mg, 99%). 1H NMR (CDCl3) δ 7.39-7.16 (m, 5H), 6.01 (br s, 1H), 4.97 (br s, 1H), 4.33 (d, J=7.0 Hz, 1H), 4.07-3.84 (m, 2H), 3.08 (d, J=6.8 Hz, 2H), 2.20 (t, J=2.5 Hz, 1H), 1.47-1.33 (m, 9H); MS (ESI+) m/z 303.3 (M+H)+.

Sources & evidence

ORD record
ord-bc2121b840c04b13925572e865ca1887
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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