Diisopropylethylamine → 2-[[2-[1,1-Dimethylethoxycarbonylamino]thiazol-4-yl]acetylamino]-4 thiazoleacetic acid, ethyl ester

HRID 1275891Notes

Reaction equation

HRID 1275891 reaction equation
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=O)[N:12]=1)=[O:6])[CH3:3].[CH2:18]([O:20][C:21](=[O:29])[CH2:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)[CH3:19].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:17][C:2]([CH3:1])([O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([NH:28][C:25]2[S:26][CH:27]=[C:23]([CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:29])[N:24]=2)=[O:16])[N:12]=1)=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 2733179PyBroPHCID 154800062-(2-((tert-Butoxycarbonyl)amino)thiazol-4-yl)acetic acid

Product 1

HCID 867561272-[[2-[1,1-Dimethylethoxycarbonylamino]thiazol-4-yl]acetylamino]-4 thiazoleacetic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[[1,1-Dimethylethoxy]carbonylamino]-4-thiazoleacetic acid (1.7 g) (Chem. Pharm. Bull. 1993, 41, 758), 2-amino-4-thiazoleacetic acid ethyl ester (1.35 g), 4-[dimethylamino]pyridine (0.8 g) and bromo-tris(pyrrolidino)phosphonium hexafluorophosphate (3.3 g) in dry dichloromethane (50 ml) was treated with diisopropylethylamine (2.4 ml). The mixture was stirred at room temperature for 16 hours. The reaction mixture was quenched with aqueous sodium bicarbonate and diluted with ethyl acetate. The organic solution was washed with brine and 2M HCl. The solution was dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 30% ethyl acetate in isohexane. Yield 0.8 g.

Workup

  1. customThe reaction mixture was quenched with aqueous sodium bicarbonate
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with brine and 2M HCl
  4. dry with materialThe solution was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-e0a86eb5907b4c8f822065f8ef6042c5
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

Loading…