1-Ethynylcyclohexylamine → (S)-2-(7-((1-aminocyclohexyl)ethynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

HRID 514100Notes

Reaction equation

HRID 514100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14](OS(C(F)(F)F)(=O)=O)=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:26])[C:9]=2[C@H:27]([OH:33])[C:28]([O:30]CC)=[O:29])=[CH:4][CH:3]=1.[BH4-].[Na+].BrC1C=[C:45]2[C:40]([CH:41]=C(C)C(C(=O)C(OCC)=O)=C2C2C=CC(Cl)=CC=2)=[CH:39]C=1.[C:62]([C:64]1([NH2:70])[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]1)#[CH:63]>>[NH2:70][C:64]1([C:62]#[C:63][C:15]2[CH:16]=[C:17]3[C:12]([CH:11]=[C:10]([CH3:26])[C:9]([C@H:27]([O:33][C:40]([CH3:45])([CH3:41])[CH3:39])[C:28]([OH:30])=[O:29])=[C:8]3[C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:13][CH:14]=2)[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]1

Participants

5

Reactant 4

HCID 1216911-EthynylcyclohexylamineHCID 4311764Sodium borohydrideHCID 67126218Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetateHCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 67126132(S)-2-(7-((1-aminocyclohexyl)ethynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

Procedure

(S)-2-(7-((1-Aminocyclohexyl)ethynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (100) was prepared by the method of Example 67 using the reduction method of Example 51 step 3 for (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate instead of step 5, NaBH4 step, from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate. The remainder of the sequence follows the method of Example 67 using 1-ethynylcyclohexanamine in Step 7. 1H-NMR: 400 MHz, (CD3OD) δ: 7.82 (d, J=8 Hz, 1H), 7.72 (s, 1H), 7.56 (m, 3H), 7.47 (d, J=8 Hz, 1H), 7.37 (s, 1H), 7.31 (d, J=8 Hz, 1H), 5.20 (s, 1H), 2.60 (s, 3H), 2.11 (m, 2H), 1.63-1.85 (m, 8H), 0.99 (s, 9H). LCMS-ESI+ (m/z): [M—NH2]+ calcd for C31H32ClO3: 487.2; found: 487.2.

Sources & evidence

ORD record
ord-73b149bf9323466088fde7287cc872c2
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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