Methanol → 2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid

HRID 1674547ノート

反応式

HRID 1674547 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO.[OH-].[Li+]>O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58798683methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoate

生成物 1

HCID 673287702-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid収率 89%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(S)-methyl 2-(tert-butoxycarbonyl)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)-propanoate iv (500 mg, 1.06 mmol) was dissolved in the mixed solvent system: THF (4 mL), methanol (1 mL), and water (2 mL). Powdered lithium hydroxide (250 mg, 10.4 mmol) was added. The light yellow slurry was stirred at rt for 15 h, and then concentrated in vacuo. The residue was partitioned between ether and water. The ether phase was discarded, and the aqueous phase was treated with 1 N HCl until the pH was 4. This acidic solution was extracted with ethyl acetate four times. The combined ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to give 430 mg (89%) of 2-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoic acid (Example 26) as a yellow oil. 1H NMR (CD3OD, 300 MHz) δ 1.38 (s, 9H), 1.51-1.60 (m, 2H), 1.89-1.98 (m, 2H), 3.28-3.32 (m, 2H), 3.59-3.64 (dd, J=14.95, 9.46 Hz, 1H), 3.71-3.74 (m, 1H), 4.33 (dd, J=9.61, 4.43 Hz, 1H), 4.87-4.94 (m, 2H), 5.63-5.72 (m, 1H), 7.71-7.77 (m, 3H), 8.01 (dd, J=7.48, 1.37 Hz, 1H); MS m/z 358 (M++1-Boc).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ether and water
  3. additionthe aqueous phase was treated with 1 N HCl until the pH was 4
  4. extractionThis acidic solution was extracted with ethyl acetate four times
  5. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-1ce83ba045104e4faf45be5ddeb5b70d
出典データセット
uspto-grants-2011_08
特許番号
US08003604B2

反応ノート

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