Acetic Acid → Benzyl 14-azido-3-methyl-6,9,12-trioxa-3-azatetradecyl(methyl)carbamate

HRID 625513ノート

反応式

HRID 625513 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][N:16]([CH2:27][CH:28]=O)[C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[N:30]([CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][NH:44][CH3:45])=[N+:31]=[N-:32].C(O)(=O)C>C1COCC1.C(OCC)(=O)C>[N:30]([CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][N:44]([CH3:45])[CH2:28][CH2:27][N:16]([CH3:15])[C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[N+:31]=[N-:32]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12010768Benzyl N-methyl-N-(2-oxoethyl)carbamateHCID 59887697Methylamino-PEG3-azide

生成物 1

HCID 86706004Benzyl 14-azido-3-methyl-6,9,12-trioxa-3-azatetradecyl(methyl)carbamate収率 58.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium triacetoxyborohydride (3.55 g, 16.8 mmol) was added portionwise at room temperature to benzyl methyl(2-oxoethyl)carbamate (2.68 g, 12.9 mmol), 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)-N-methylethanamine 222c (3.00 g, 12.9 mmol), and acetic acid (2 equiv.) in THF (20 mL). The mixture was stirred for 2 hours, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried (Mg2SO4) and evaporated. The residue was purified by Combiflash purification system (ethyl acetate/dichloromethane) to give product as an oil (3.19 g, 58%); MS (ES, m/z): 424 [M+H]+.

後処理

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (Mg2SO4)
  3. customevaporated
  4. customThe residue was purified by Combiflash purification system (ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-c8af1cccb72d47ca94217cb1c8609d32
出典データセット
uspto-grants-2016_04
特許番号
US09301951B2

反応ノート

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