1,2-Dichloroethane → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1371520ノート

反応式

HRID 1371520 の反応式
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22]OCN.C(Cl)CCl.C1C=C[C:33]2[N:38]([OH:39])N=NC=2C=1.CCN(C(C)C)C(C)C>C(OCC)(=O)C.C1COCC1>[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([N:38]([O:39][CH3:22])[CH3:33])=[O:13]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 21959107Methoxymethanamine hydrochloride

生成物 1

HCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate収率 71.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Boc-D-Tic-OH (14.9 g, 53.7 mmol), methoxymethylamine hydrochloride (5.24 g, 53.7 mmol), EDC (11.3 g, 59.1 mmol); HOBT (7.98 g, 59.1 mmol), DIPEA (9.83 ml, 59.1 mmol) and THF (500 ml) are combined, and the resulting mixture is stirred for about 18 hours at r.t. under nitrogen. The mixture is stripped to dryness, and the residue is taken up in ethyl acetate. The resulting mixture is washed with 1M HCl, saturated NaHCO3 and brine, and then dried. Solvent is removed and the residue is chromatographed on normal phase using 1:1 ethylacetate/hexane to give about 12.3 g of Boc-D-Tic-NMeOMe (Weinreb amide).

後処理

  1. washThe resulting mixture is washed with 1M HCl, saturated NaHCO3 and brine
  2. customdried
  3. customSolvent is removed
  4. customthe residue is chromatographed on normal phase

出典と根拠

ORDレコード
ord-b5ebed1fb6df4e2680ba4587046d7198
出典データセット
uspto-grants-2007_01
特許番号
US07157463B2

反応ノート

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