Benzoyl chloride → HCID 15409402, compound

HRID 397028Notes

Reaction equation

[C:1]([N:9]([C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:27][CH2:26][C@@H:24]([OH:25])[C@@H:22]([OH:23])[C@H:20]1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:36](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:28]([N:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:27][CH2:26][C@@H:24]([OH:25])[C@@H:22]([OH:23])[C@H:20]1[O:21][C:36](=[O:37])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: -88.5 °C

Procedure

26.4 g (55,5 mmol) of 3 were dissolved in 550 ml of anhydrous CH2Cl2 and 55 ml of pyridine (in each case stored over a molecular sieve) under an N2 atmosphere, treated with 0.73 g (5.55 mmol; 0.1 eq.) of DMAP and cooled to −87 to −90° C. 8.58 g (61 mmol; 1.1 eq.) of BzCl in 14 ml of pyridine were added dropwise in the course of 1 h and the mixture was left at −78° C. over a period of 60 h (week-end). The batch was concentrated, treated twice with 100 ml of toluene each time and evaporated in order to remove pyridine. Chromatography on silica gel 60 (20×10 cm) using gradients (AcOEt/heptane, 1:1 to 9:1) yielded 23.2 g of 4.

Workup

concentrationThe batch was concentrated
additiontreated twice with 100 ml of toluene each time
customevaporated in order
customto remove pyridine

Sources & evidence

ORD record: ord-775fc049cfe1435f923993006c88eefa
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608186B1

Reaction notes

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