Hydrochloric Acid → HCID 18596139, compound

HRID 615347Notes

Reaction equation

HRID 615347 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][S:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:17](Cl)(=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24].Cl>C(=O)([O-])[O-].[Na+].[Na+].O>[C:17]([N:13]1[C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][S:10][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)(=[O:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:13]1[C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][S:10][CH:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1)=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 67341Pimeloyl chlorideHCID 13553596HCID 13553596, compound

Product 1

HCID 18596139HCID 18596139, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of (4R)-2-(3-cyanophenyl)-4-thiazolidinecarboxylic acid (4.7 g) in 1M sodium carbonate (30 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 30 minutes at the same temperature, and filtered to give the precipitates. The precipitates were dissolved in hot water (100 ml), and acidified with concentrated hydrochloric acid. The separated crystals were collected by filtration to give 3.5 g (59%) of the titled compound: mp 105°-112° C.; [α]D25 +115.0° (c=1.0, methanol). IR (nujol, cm-1): 2270 (CN), 1735 (COOH), 1640 (CON), 1610 (aromatic), 1195, 790 (aromatic). NMR (DMSO-d6) δ: 0.69-1.66 (6H, m, --CH2 --CH2)3CH2 --), 1.70-2.50 (4H, m, --CH2 --CH2)3CH2 --), 2.85-3.66 (4H, m, C5 --H), 4.69 (1H, dd, J=8.2, 6.0 Hz, C4 --H), 5.13 (1H, m, C4 --H), 6.16 (1H, s, C2 --H), 6.43 (1H, s, C2 -- H), 7.3-8.3 (8H, m, arom. H). TLC: Rf value* 0.33.

Workup

  1. temperaturecooling
  2. filtrationfiltered
  3. customto give the precipitates
  4. filtrationThe separated crystals were collected by filtration

Sources & evidence

ORD record
ord-f6fea516084b4cddb86a5390d4a4f2e5
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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