1-Aminotetralin, (S)- → [(S)-1-((S)-2-{(2S,4S)-4-Amino-2-[(S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-1-yl}-1-cyclohexyl-2-oxo-ethylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester

HRID 1481924Notes

Reaction equation

HRID 1481924 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([C@H:9]([C:11](=[O:38])[NH:12][C@@H:13]([CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C:14]([N:16]1[CH2:20][C@@H:19]([NH2:21])[CH2:18][C@H:17]1[C:22](=[O:31])[NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:40](OC(N(C)[C@@H](C)C(N[C@@H](C1CCCCC1)C(N1C[C@@H](NC(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)C[C@H]1C(O)=O)=O)=O)=O)(C)([CH3:42])[CH3:41].[C@@H]1(N)C2C(=CC=CC=2)CCC1>>[C:1]([O:5][C:6](=[O:39])[N:7]([C@H:9]([C:11](=[O:38])[NH:12][C@@H:13]([CH:32]1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1)[C:14]([N:16]1[CH2:20][C@@H:19]([NH2:21])[CH2:18][C@H:17]1[C:22](=[O:31])[NH:23][C@@H:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:42][CH2:40][CH2:41]1)=[O:15])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 70580741-Aminotetralin, (S)-HCID 90231415(2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid2×HCID 90231684{(S)-1-[(S)-2-((2S,4S)-4-Amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester2×

Product 1

HCID 90231663[(S)-1-((S)-2-{(2S,4S)-4-Amino-2-[(S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamoyl]-pyrrolidin-1-yl}-1-cyclohexyl-2-oxo-ethylcarbamoyl)-ethyl]-methyl-carbamic acid tert-butyl ester

Procedure

In a similar manner to that described for {(S)-1-[(S)-2-((2S,4S)-4-amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (Intermediate 28), (2S,4S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid (Intermediate 27) (150 mg, 0.22 mmol) and (S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine (Aldrich) (33 mg, 0.22 mmol) were converted to the title compound (48 mg, foam).

Sources & evidence

ORD record
ord-82d197a30f084f459459f7feaa32cf16
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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