Triethylamine → (S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

HRID 851439Notes

Reaction equation

HRID 851439 reaction equation
[CH2:1]([O:3][P:4]([CH2:16][C:17]([OH:19])=O)([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.Cl.[S:40]1[C:44]2([CH2:48][CH:47]([C:49]([OH:51])=[O:50])[NH:46][CH2:45]2)[S:43][CH2:42][CH2:41]1>C(#N)C>[CH2:1]([O:3][P:4]([CH2:16][C:17]([N:46]1[C@H:47]([C:49]([OH:51])=[O:50])[CH2:48][C:44]2([S:40][CH2:41][CH2:42][S:43]2)[CH2:45]1)=[O:19])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13136848[Ethoxy(4-phenylbutyl)phosphoryl]acetic acidHCID 453580021,4-Dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, hydrochloride

Product 1

HCID 54496794(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2.0 g of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid and 1.1 g of carbonyldiimidazole in acetonitrile is stirred under argon at 0° C. for 1 hour and then treated with 1.9 g of triethylamine and 1.7 g of 1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, hydrochloride. After 4.5 hours the acetonitrile is stripped and the residue is partitioned between ethyl acetate and 1 N HCl. The organic phase is washed with brine, dried (MgSO4), and the solvent is stripped to give 3.2 g of the title compound as an oil.

Workup

  1. customthe residue is partitioned between ethyl acetate and 1 N HCl
  2. washThe organic phase is washed with brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-4abc22619124421bbab91d1e4ddadf01
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

Loading…