Pimeloyl chloride → HCID 12837236, compound

HRID 615348Notes

Reaction equation

HRID 615348 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[NH:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][S:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:18](Cl)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C(=O)([O-])[O-].[Na+].[Na+]>[C:18]([N:14]1[C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][S:11][CH:10]1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([N:14]1[C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][S:11][CH:10]1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:25]

Participants

4

Reactant 2

HCID 67341Pimeloyl chlorideHCID 2787521HCID 2787521, compound

Product 1

HCID 12837236HCID 12837236, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of (4R)-2-(3-nitrophenyl-4-thiazolidinecarboxylic acid (5.1 g) in 1M sodium carbonate (40 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 1 hour at the same temperature, and the separated crystals were filtered to give 4.7 g (69%) of the titled compound as disodium salt: mp 111°-113° C. (dec.) (water); [α]D25 +88.2° (c=0.5, methanol). IR (nujol, cm-1): 1635 (CON), 1585 (COO-), 1520 and 1355 (NO2), 1095, 730. TLC: Rf value* 0.28.

Workup

  1. temperaturecooling
  2. filtrationthe separated crystals were filtered

Sources & evidence

ORD record
ord-9256edbc0ffa45668c243ed0311614c7
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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