Ethanol → (-)-6-[(4-chlorophenyl)-hydrazinomethyl]-1-methyl-1H-benzotriazole (R)-alpha-hydroxybenzeneacetate

HRID 1288620Notes

Reaction equation

[ClH:1].ClC1C=CC([NH:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=CC=1.C(O)C.[OH-].[Na+].[OH:27][C@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29]([OH:31])=[O:30]>O>[OH:27][C@H:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29]([OH:31])=[O:30].[Cl:1][C:32]1[CH:37]=[CH:36][C:35]([CH:11]([NH:10][NH2:9])[C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 14 °C

Procedure

To a mixture of 200 g of intermediate 2-a and 479 ml of ethanol at 23° C. was added a solution of 23.94 g of sodium hydroxide in 180 ml of water. After stirring for 10 min. there were added 50.2 g of (-)-(R)α-hydroxybenzeneacetic acid. The whole was stirred for 30 min. at 60° C. and the product was crystallized by adding some product crystals obtained in a previous low-scale set-up. Then the whole was stirred for 2 hours at 50° C. and overnight at room temperature. The reaction mixture was cooled (temp.14° C.) and stirred for 1 hour. The product was filtered off, washed with ethanol and dried in vacuo, yielding 118.8 g (87%) of (±)-6-[(4-chlorophenyl)-hydrazinomethyl]-1-methyl-1H-benzotriazole (R)-α-hydroxybenzeneacetate (1:1) monohydrate (interm. 3-a); diastereomeric excess: 92.6%.

Workup

stirringThe whole was stirred for 30 min. at 60° C.
customthe product was crystallized
additionby adding some product crystals
customobtained in a previous low-scale set-up
stirringThen the whole was stirred for 2 hours at 50° C. and overnight at room temperature
stirringstirred for 1 hour
filtrationThe product was filtered off
washwashed with ethanol
customdried in vacuo

Sources & evidence

ORD record: ord-d8fced3eccc44705baa6b81d3d8251c0
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05746840

Reaction notes

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