反応 #1994336

ord-c694192eb162495f89d0893a612dc0e1

反応方程式

Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](CCCCC(C)C(=O)O)C(=O)NCCCc1ccccc1
methyl (7R)-7-{[N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl]amino}-8-oxo-8-[(3-phenylpropyl)amino]octanoic acid
[Li+].[OH-]
lithium hydroxide
O
water
Cc1cc(O)cc(C)c1C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@H](CCCCCC(=O)O)C(=O)NCCCc1ccccc1
(7R)-7-{[N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl]amino}-8-oxo-8-[(3-phenylpropyl)amino]octanoic acid

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他Volatiles were evaporated
  2. 2
    抽出Product was extracted with ethyl acetate
  3. 3
    抽出the organic extract
  4. 4
    洗浄washed with brine
  5. 5
    乾燥dried over MgSO4
  6. 6
    濃縮concentrated to a fine white solid which
  7. 7
    その他was taken directly into boc deprotection (preparation 28) on basis of LRMS m/z 598 [M+H]

実験手順

To a solution of methyl (7R)-7-{[N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl]amino}-8-oxo-8-[(3-phenylpropyl)amino]octanoic acid (400 mg, 0.65 mmol) from preparation 14 in 3 ml dry THF was added a 0.5M solution of lithium hydroxide in water (3 ml, 1.5 mmol) and the reaction mixture stirred at rt overnight. Volatiles were evaporated and the residue acidified with 0.5M KHSO4. Product was extracted with ethyl acetate and the organic extract washed with brine, dried over MgSO4 and concentrated to a fine white solid which was taken directly into boc deprotection (preparation 28) on basis of LRMS m/z 598 [M+H].

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08598123B2uspto-grants-2013_12