(1R)-2-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid → HCID 86708775, compound

HRID 1751567Notes

Reaction equation

HRID 1751567 reaction equation
[CH3:1][O:2][C:3](=[O:65])[NH:4][C@@H:5]([CH:62]([CH3:64])[CH3:63])[C:6]([N:8]1[C@H:16]([C:17]2[NH:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4C=C[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([C:38]6[NH:42][C:41]([C@@H:43]7[CH2:47][CH2:46][CH2:45][N:44]7[C:48](=[O:61])[C@H:49]([NH:56][C:57]([O:59][CH3:60])=[O:58])[C:50]7[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=7)=[N:40][CH:39]=6)[CH:34]=5)[CH:29]=4)=[CH:24][CH:23]=3)=[CH:20][N:21]=2)[CH2:15][C:10]2(OCCO2)[CH2:9]1)=[O:7].Cl.Cl.Cl.CC(C)[C@H](NC(=O)OC)C(=O)N1CCC[C@H]1C1NC([C:83]2[CH:92]=[CH:91][C:90]3[C:85](=CC=C(C4C=CC(C5NC([C@@H]6CCCN6)=NC=5)=CC=4)C=3)[CH:84]=2)=CN=1.[CH2:116](OC(N1CCC2C(=CC=CC=2)[C@@H]1C(O)=O)=O)[C:117]1C=CC=CC=1.COC(N[C@H:144](C1C=CC=CC=1)[C:145](O)=O)=O.Cl.Cl.Cl.CC(C)[C@H](NC(=O)OC)C(=O)N1[C@H](C2NC(C3C=CC(C4C=CC5C(=CC=C(C6NC([C@@H]7CCCN7)=NC=6)C=5)C=4)=CC=3)=CN=2)CC2(OCCO2)C1>>[CH3:1][O:2][C:3]([NH:4][C@@H:5]([CH:62]([CH3:64])[CH3:63])[C:6]([N:8]1[CH2:9][CH2:10][CH2:15][C@H:16]1[C:17]1[NH:18][C:19]([C:22]2[CH:27]=[C:26]3[C:25](=[CH:24][CH:23]=2)[CH:28]=[C:29]([C:30]2[CH:31]=[CH:32][C:33]([C:38]4[NH:42][C:41]([C@@H:43]5[CH2:47][CH2:46][CH2:45][N:44]5[C:48]([C@H:49]5[C:50]6[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=6)[CH2:145][CH2:144][N:56]5[C:57]([O:59][CH2:60][C:83]5[CH:92]=[CH:91][CH:90]=[CH:85][CH:84]=5)=[O:58])=[O:61])=[N:40][CH:39]=4)=[CH:34][CH:35]=2)[CH:117]=[CH:116]3)=[CH:20][N:21]=1)=[O:7])=[O:65]

Participants

5

Reactant 4

HCID 40787014(1R)-2-[(Benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acidHCID 69675210HCID 69675210, compoundHCID 131733633HCID 131733633, compoundHCID 131733634HCID 131733634, compound

Product 1

HCID 86708775HCID 86708775, compound

Procedure

The title compound was prepared according to the method employed to prepare (S)-1-((S)-8-(5-(4-(6-(2-((S)-1-((R)-2-(methoxycarbonylamino)-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester, except that methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(6-(4-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate 3HCl salt and (R)-2-(benzyloxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid were used instead of, respectively, methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate 3HCl salt (R)-2-(methoxycarbonylamino)-2-phenylacetic acid. MS (ESI) m/z 841.83 [M+H]+. (135 mg, 99%).

Sources & evidence

ORD record
ord-ac3e5da10c574e3595b6da0965cdef8c
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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