Diisopropylethylamine → Ethyl (R) 3-{4-[2-(4-methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoate

HRID 1357860Notes

Reaction equation

HRID 1357860 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:25][O:26][C:27]1[C:32]2[N:33]=[C:34]([NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH3:43])[O:35][C:31]=2[CH:30]=[C:29]([CH2:44][C:45](O)=[O:46])[CH:28]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[CH3:25][O:26][C:27]1[C:32]2[N:33]=[C:34]([NH:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH3:43])[O:35][C:31]=2[CH:30]=[C:29]([CH2:44][C:45]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@H:8]([CH3:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)=[O:46])[CH:28]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 181881002-(4-Methoxy-2-o-tolylaminobenzoxazol-6-yl)acetic acidHCID 53963459HCID 53963459, compound

Product 1

HCID 86585957Ethyl (R) 3-{4-[2-(4-methoxy-2-o-tolylaminobenzoxazol-6-yl)acetylamino]phenyl}butanoateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of with ethyl (R) 3-(4-aminophenyl)butanoate (0.107 g, Reference Example 1) in dimethylformamide (10 mL) was treated with diisopropylethylamine (0.4 g), 2-(4-methoxy-2-o-tolylaminobenzoxazol-6-yl)acetic acid [0.105 g, Reference Example 9(a)] and then with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.14 g). The mixture was left to stand for 20 hours and then partitioned between ethyl acetate and hydrochloric acid (1M). The organic phase was washed with water, then with aqueous bicarbonate solution (5%), then with water, then with brine, then dried and then evaporated to give the title compound (0.17 g) as a cream coloured solid.

Workup

  1. waitThe mixture was left
  2. custompartitioned between ethyl acetate and hydrochloric acid (1M)
  3. washThe organic phase was washed with water
  4. dry with materialwith aqueous bicarbonate solution (5%), then with water, then with brine, then dried
  5. customevaporated

Sources & evidence

ORD record
ord-c59a1605500a4370b225f4b99379efa6
Source dataset
uspto-grants-2003_07
Patent number
US06593354B2

Reaction notes

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