1-Hydroxybenzotriazole → tert-Butyl methylcarbamate

HRID 1668418ノート

反応式

HRID 1668418 の反応式
[C:1]([O:5][C:6]([N:8](C)[C@@H:9](CC)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.C(NC([C@H]1N2C(=O)[C@@H](N)CCC(=O)N2CCC1)=O)CC1C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOCC>[C:1]([O:5][C:6](=[O:7])[NH:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15689337(2S)-2-(((1,1-Dimethylethoxy)carbonyl)methylamino)butanoic acidHCID 57612839HCID 57612839、化合物

生成物 1

HCID 527635tert-Butyl methylcarbamate収率 267.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of (S)-2-(tert-butoxycarbonyl-methyl-amino)-butyric acid (167 mg, 0.77 mmol) in DMF (5 mL) at room temperature, is added diisopropylethylamine (0.48 mL) slowly. After stirring at room temperature for 20 minutes, the solution is transferred to another flask contained (1S,9S)-9-amino-6,10-dioxo-octahydro-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid phenethyl-amide (240 mg, 0.70 mmol), and then a solution of HOBT (125 mg, 0.92 mmol) and HBTU (350 mg, 0.92 mmol) in DMF (5 mL) is added to the reaction mixture. After stirring for 1.5 hours, the reaction solution is diluted with ether (20 mL), and washed with water (2×10 mL). The combined organic layers is concentrated. The crude product is diluted with CH2Cl2 (10 mL) and dried over Na2SO4, and purified by chromatography (CH2Cl2/MeOH:97/3) to give (S)-1-((4S,7S)-6,10-dioxo-4-phenethylcarbamoyl-octahydro-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamoyl)-propyl]-methyl-carbamic acid tert-butyl ester (270 mg, 71.3%) as pale solid. (NMR and MS data confirmed, U-3133-69).

後処理

  1. customthe solution is transferred to another flask
  2. stirringAfter stirring for 1.5 hours
  3. washwashed with water (2×10 mL)
  4. concentrationThe combined organic layers is concentrated
  5. additionThe crude product is diluted with CH2Cl2 (10 mL)
  6. dry with materialdried over Na2SO4
  7. custompurified by chromatography (CH2Cl2/MeOH:97/3)

出典と根拠

ORDレコード
ord-d9dfa86695e641d4b0f9e75d3a448e99
出典データセット
uspto-grants-2011_08
特許番号
US07989441B2

反応ノート

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