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Formic Acid → Boc-Leu-Leu-Lys(Z)-Leu-Leu-OH

HRID 2298449
ノート
印刷プレビュー

反応式

HRID 2298449 の反応式
[OH-].[Na+].[NH:3]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:4]([C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:52]([O:54]C)=[O:53])[CH2:48][CH:49]([CH3:51])[CH3:50])=[O:45])[CH2:40][CH:41]([CH3:43])[CH3:42])=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH2:5][CH:6]([CH3:8])[CH3:7].C1COCC1.C(O)=O>O.C(OCC)(=O)C>[NH:3]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[C@H:4]([C:9]([NH:11][C@H:12]([C:17]([NH:19][C@H:20]([C:36]([NH:38][C@H:39]([C:44]([NH:46][C@H:47]([C:52]([OH:54])=[O:53])[CH2:48][CH:49]([CH3:50])[CH3:51])=[O:45])[CH2:40][CH:41]([CH3:42])[CH3:43])=[O:37])[CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[CH2:5][CH:6]([CH3:8])[CH3:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12020547Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe

生成物 1

HCID 12020548Boc-Leu-Leu-Lys(Z)-Leu-Leu-OH収率 97.5%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
62.5 °C

実験手順

A solution of NaOH(1.44 g, 36.0 mmol) in H2O (15.0 g) was added at 20-25° C. over 5 min to a mixture of Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe (SEQ. ID No. 2) (12.0 g, 14.16 mmol) THF (48.0 g) and H2O (18.0 g). The resulting mixture was stirred for 2 h. 98% Formic acid (5 g) was added, followed by ethyl acetate (30.0 g). The resulting organic phase was washed with H2O, concentrated in vacuo and the residue was dissolved in MeOH (60.0 g). The solids were filtered and rinsed with an additional portion of MeOH (8.0 g). The combined MeOH solution was heated to 60-65° C. and H2O (30.0 g) was added over 10 min. This mixture was cooled to 20-25° C., the solid product began to crystallize. An additional portion of H2O (35.0 g) was added and the mixture was stirred for 1 h. The solid product was filtered, washed with H2O and dried in vacuo to give Boc-Leu-Leu-Lys(Z)-Leu-Leu-OH (SEQ. ID No. 2) (11.5 g, 97.5%).

後処理

  1. washThe resulting organic phase was washed with H2O
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue was dissolved in MeOH (60.0 g)
  4. filtrationThe solids were filtered
  5. washrinsed with an additional portion of MeOH (8.0 g)
  6. additionH2O (30.0 g) was added over 10 min
  7. temperatureThis mixture was cooled to 20-25° C.
  8. customto crystallize
  9. additionAn additional portion of H2O (35.0 g) was added
  10. stirringthe mixture was stirred for 1 h
  11. filtrationThe solid product was filtered
  12. washwashed with H2O
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-a24bf1aa912b47238f6d0e91d53a75d4
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06492490B1

反応ノート

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