(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid → tert-Butyl ((S)-1-(((S)-3,3-dimethyl-1-((S)-7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate

HRID 339254Notes

Reaction equation

HRID 339254 reaction equation
[C@H]1(N[C:12]([C@@H:14]2[CH2:23]C3C(=CC(OS(C(F)(F)F)(=O)=O)=CC=3)[CH2:16][N:15]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:13])C2C(=CC=CC=2)CCC1.[NH2:39][C@@H:40]([C:69]([CH3:72])([CH3:71])[CH3:70])[C:41]([N:43]1[C@H:52]([C:53]([NH:55][C@H:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH2:59][CH2:58][CH2:57]2)=[O:54])[CH2:51][C:50]2[C:45](=[CH:46][C:47]([N+:66]([O-:68])=[O:67])=[CH:48][CH:49]=2)[CH2:44]1)=[O:42].C(OC(N(C)[C@@H](C)C(O)=O)=O)(C)(C)C>>[CH3:70][C:69]([CH3:72])([CH3:71])[C@H:40]([NH:39][C:12](=[O:13])[C@@H:14]([N:15]([CH3:16])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH3:23])[C:41]([N:43]1[C@H:52]([C:53](=[O:54])[NH:55][C@H:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[CH2:59][CH2:58][CH2:57]2)[CH2:51][C:50]2[C:45](=[CH:46][C:47]([N+:66]([O-:68])=[O:67])=[CH:48][CH:49]=2)[CH2:44]1)=[O:42]

Participants

4

Reactant 3

HCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 86705865(S)-tert-butyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-7-(((trifluoromethyl)sulfonyl)oxy)-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 86705893(S)-2-((S)-2-amino-3,3-dimethylbutanoyl)-7-nitro-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

Product 1

HCID 86705892tert-Butyl ((S)-1-(((S)-3,3-dimethyl-1-((S)-7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamateYield 97%

Procedure

Following a procedure analogous to that for the synthesis of Compound D, (S)-2-((S)-2-amino-3,3-dimethylbutanoyl)-7-nitro-N—((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (2.17 g, 4.67 mmol) and (S)-2-((tert-butoxycarbonyl)(methyl)amino)propanoic acid (Advanced ChemTech, 0.95 g, 4.67 mmol) were converted to the title compound (2.93 g, 97%). MS (ESI+) m/z 650.5 (M+H)+.

Sources & evidence

ORD record
ord-5145be7d8c58417c9b3cc1187892a9ff
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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