L-Lysine → HCID 68627743, compound

HRID 2070591Notes

Reaction equation

HRID 2070591 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][CH2:8][C:7]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([C@H:19]([C:24]#[C:25][CH3:26])[CH2:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=3)=[CH:6]2)[CH2:4][CH2:3][CH2:2]1.[NH2:27][C@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33]>CC(O)C.O>[NH2:27][C@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33].[CH2:4]1[C:5]2([CH2:10][CH2:9][CH2:8][C:7]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([C@H:19]([C:24]#[C:25][CH3:26])[CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:18]=3)=[CH:6]2)[CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 5962L-LysineHCID 57771434HCID 57771434, compound

Product 1

HCID 68627743HCID 68627743, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of (R)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid (5.0 g) obtained in Example 93 in 2-propanol (75 mL) was added a solution of L-lysine (2.07 g) in water (5.75 mL) at 70° C., followed by stirring overnight while gradually cooling the mixture down to room temperature. The precipitate was filtered and then dried to give (R)-3-[4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid L-lysine salt (5.64 g).

Workup

  1. filtrationThe precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-3365bb53d0ae486eb98122899277dab8
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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