Isopropyl chloroformate → 3-{2-(2-Isopropoxycarbonylamino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid

HRID 1181087Notes

Reaction equation

HRID 1181087 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH2:27][CH2:28][NH2:29].Cl[C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33]>C(Cl)Cl>[CH:35]([O:34][C:32]([NH:29][CH2:28][CH2:27][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:30])=[O:2])=[O:33])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 7917Isopropyl chloroformateHCID 589790753-{2-(2-Amino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester

Product 1

HCID 102060633-{2-(2-Isopropoxycarbonylamino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{2-(2-amino-ethyl)-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid methyl ester (26 mg, 0.064 mmol) in CH2Cl2 (2 mL) at 0° C. was treated with TEA (0.2 mL) and isopropyl chloroformate (0.13 mL, 1.0 M in ether). The resulting mixture was allowed to warm gradually to ambient temperature. After 2 h, the mixture was concentrated to a residue, which was purified by silica gel chromatography (hexanes/EtOAc 7/3) to afford the isopropyl carbamate as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.19 (d, 6H, J=5.9 Hz), 2.42 (s, 3H), 2.54 (t, 2H, J=7.8 Hz), 2.79 (t, 2H, J=6.8 Hz), 2.89 (t, 2H, J=7.8 Hz), 3.05 (br s, 2H), 3.38 (br s, 2H), 3.60 (s, 3H), 4.26 (t, 2H, J=6.8 Hz), 4.68 (br s, 1H), 4.89 (q, 1H, J=6.4 Hz), 6.70 (br s, 1H), 6.71 (d, 1H, J=8.3 Hz), 7.05 (d, 1H, J=8.3 Hz), 7.47 (m, 3H), 8.10 (m, 2H).

Workup

  1. concentrationthe mixture was concentrated to a residue, which
  2. customwas purified by silica gel chromatography (hexanes/EtOAc 7/3)

Sources & evidence

ORD record
ord-87879d5b043e481a836d91f9751de35c
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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