1,2-Dichloroethane → Boc-D-cyclohexylglycine proline methyl ester

HRID 482554ノート

反応式

HRID 482554 の反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=[O:17])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].Cl.[CH3:20][O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.O>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:16]([OH:18])=[O:17])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7])([CH3:1])[CH3:3].[CH3:20][O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2733200methyl L-prolinate hydrochlorideHCID 7014890(2R)-2-(((tert-butoxy)carbonyl)amino)-2-cyclohexylacetic acid

生成物 1

HCID 131720805Boc-D-cyclohexylglycine proline methyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 8.0 g (31.0 mmol)of Boc-D-cyclohexylglycine and 5.8 g (35 mmol) of proline methyl ester HCl salt in 100 ml of anh. DMF, mixed with 5.8 g (37.2 mmol) of HOBt with the pH adjusted to 7-8 with N-methylmorpholine (to moistened narrow-range pH paper), was treated with 7.9 g (40.3 mmol) of EDC and stirred for 18 hr in a nitrogen atmosphere. After 20 hr water (10 ml) was added, the solution concentrated in vacuo and partitioned with 400 ml EtOAc and 200 ml H2O, washing with dil. NaHCO3, H2O, dil. KHSO4, and twice with 50% satd NaCl, dried over Na2SO4 and concentrated under reduced pressure to give an oil. This crude material was chromatographed on 300 g silica gel in 1:1 (v/v) EtOAc/hexane to afford, after pooling of fractions, intermediary 26-1.

後処理

  1. concentrationthe solution concentrated in vacuo
  2. custompartitioned with 400 ml EtOAc and 200 ml H2O
  3. washwashing with dil. NaHCO3, H2O, dil. KHSO4
  4. dry with materialtwice with 50% satd NaCl, dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. customThis crude material was chromatographed on 300 g silica gel in 1:1 (v/v) EtOAc/hexane
  8. customto afford

出典と根拠

ORDレコード
ord-5a569b9e33a843c89b30e1b744d43e9c
出典データセット
uspto-grants-1998_08
特許番号
US05798377

反応ノート

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