Triethylamine → Diisopropyl Ether

HRID 2289821Notes

Reaction equation

HRID 2289821 reaction equation
[C:1]([O:5][C:6](=[O:36])[C@H:7]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:23])=[CH:17][N:18]=[C:19]2[Cl:22])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].Cl[C:38]1C2C(=CC=C(S(Cl)(=O)=O)C=2)C(Cl)=CN=1.Cl.C(OC(=O)[C@H](CCCCN)NC(OC(C)(C)C)=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[O:5]([CH:1]([CH3:3])[CH3:4])[CH:6]([CH3:7])[CH3:38].[C:1]([O:5][C:6](=[O:36])[C@H:7]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([C:16]([Cl:23])=[CH:17][N:18]=[C:19]2[Cl:22])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 166582941,4-Dichloroisoquinoline-7-sulfonyl chlorideHCID 21969824Nalpha-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl esterHCID 513584377750-45-0

Product 2

HCID 7914Diisopropyl EtherHCID 21969824Nalpha-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-Nepsilon-tert-butyloxycarbonyl-L-lysine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nα-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-Nε-tert-butyloxycarbonyl-L-lysine tert-butyl ester ##STR190## A solution of 1,4-dichloro-7-isoquinolinylsulphonyl chloride (250 mg, 0.84 mmol), Ne-tert-butyloxycarbonyl-L-lysine tert-butyl ester hydrochloride (286 mg, 0.84 mmol) and triethylamine (235 μl, 1.69 mmol) in CH2Cl2 (25 ml) was stirred at 23° C. for 3h. The reaction mixture was washed with water (2×20 ml), dried (MgSO4) and concentrated in vacuo to a residue which upon trituration with hexane and then i-Pr2O gave Nα-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-Nε-tert-butyloxycarbonyl-L-lysine tert-butyl ester as a white powder (270 mg, 0.48 mmol).

Workup

  1. washThe reaction mixture was washed with water (2×20 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo to a residue which upon trituration with hexane

Sources & evidence

ORD record
ord-f0bce4b963bb48e8bdb4bbce261066aa
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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