3-Butyn-2-amine, 2-methyl- → (S)-2-(7-(3-amino-3-methylbut-1-ynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

HRID 514098Notes

Reaction equation

HRID 514098 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.[CH3:62][C:63]([NH2:67])([C:65]#[CH:66])[CH3:64]>>[NH2:67][C:63]([CH3:64])([CH3:62])[C:65]#[C:66][C:15]1[CH:16]=[C:17]2[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]2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 4

HCID 763193-Butyn-2-amine, 2-methyl-HCID 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 67126318(S)-2-(7-(3-amino-3-methylbut-1-ynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

Procedure

(S)-2-(7-(3-Amino-3-methylbut-1-ynyl)-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (98) 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 2-methylbut-3-yn-2-amine in Step 7. 1H-NMR: 400 MHz, (CD3OD) δ: 7.81 (d, J=8 Hz, 1H), 7.72 (s, 1H), 7.57 (m, 3H), 7.45 (d, J=8 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J=8 Hz, 1H), 5.16 (s, 1H), 2.62 (s, 3H), 1.68 (s, 6H), 0.98 (s, 9H). LCMS-ESI+ (m/z): [M—NH2]calcd for C28H28ClO3: 447.2; found: 446.9.

Sources & evidence

ORD record
ord-46ae3329f1c34f4a8407671873fb72c1
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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