Diisopropylethylamine → HCID 10717980, compound

HRID 275997Notes

Reaction equation

[NH2:1][C@@H:2]([CH3:12])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[OH:4].Br[CH2:14][CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([NH:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:18]([Cl:30])[CH:17]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:22][C:20]1[CH:21]=[C:16]([CH2:15][CH2:14][NH:1][C@@H:2]([CH3:12])[C@H:3]([OH:4])[C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=2)[CH:17]=[C:18]([Cl:30])[C:19]=1[NH:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (1R,2S)-2-amino-1-(4-hydroxyphenyl)-propan-1-ol (495 mg) and ethyl N-[4-(2-bromoethyl)-2,6-dichloro-phenyl]aminoacetate (700 mg) in N,N-dimethylformamide (6 ml) was added N,N-diisopropylethylamine (343 μl), and the mixture was stirred for 7 hours at 70° C. The reaction mixture was concentrated in vacuo, and purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloro-methane/ethanol=20/1) gave ethyl N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]-ethyl]phenyl]aminoacetate (510 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo, and purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: dichloro-methane/ethanol=20/1)

Sources & evidence

ORD record: ord-7438128c5ca244b7bec72958614874a5
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353025B1

Reaction notes

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