Acetic acid, (p-butoxyphenyl)- → N-[(4-butoxyphenyl)acetyl)-D-allo-Threonine

HRID 52248

Reaction equation

HRID 52248 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:16][C@@H:17]([C:21]([OH:23])=[O:22])[C@@H:18]([CH3:20])[OH:19]>>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([NH:16][C@@H:17]([C:21]([OH:23])=[O:22])[C@@H:18]([CH3:20])[OH:19])=[O:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 78304Acetic acid, (p-butoxyphenyl)-HCID 90624D-Allothreonine

Product 1

HCID 22851679N-[(4-butoxyphenyl)acetyl)-D-allo-Threonine

Procedure

4-Butoxyphenylacetic acid (288 mg, 1.38 mmol) is converted to the acid chloride and added to D-allo-Thr (150 mg, 1.26 mmol) to get 2c-9, following the procedure described in Example 6. The crude product is purified by chromatography (2.5×18 cm column, gradient 4% CH3OH and 0.3% HOAc in CH2Cl2): NMR δ0.96 (t, J=7.4, 3H), 1.14 (d, J=5.8, 3H), 1.47 (m, 2H), 1.74 (m, 2H), 3.53 (br s, 2H), 3.91 (t, J≈6.5, 2H), 4.10 (br s, 1H), 4.53 (br s, 1H), 4.90 (br s, >2H), 6.76 (br d, J=6.0, 1H), 6.84 (d, J=8.4, 2H), 7.13 (d, J=8.4, 2H); MS (HR-E ) m/z 309.1567 (M calcd. for C16H23NO5, 309.1576); [α]D26±2 (CHCl3); m.p. 90°-94° C.

Workup

  1. customto get 2c-9
  2. customThe crude product is purified by chromatography (2.5×18 cm column, gradient 4% CH3OH and 0.3% HOAc in CH2Cl2)

Sources & evidence

ORD record
ord-ec9a6611cb5443d0b96d345b49e9226c
Source dataset
uspto-grants-1997_04
Patent number
US05616612

Linked notes

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