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Formic Acid → ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

HRID 222835
ノート
印刷プレビュー

反応式

HRID 222835 の反応式
C(N(CC)CC)C.C(O)=O.ClC1C=CC=CC=1.[C:18]([NH:37][CH:38]([C:44](=[O:60])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O>[C:18]([NH:37][C@H:38]([C@H:44]([OH:60])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]
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

6

反応物 4

HCID 284Formic AcidHCID 7964ChlorobenzeneHCID 8471TriethylamineHCID 24880587Ethyl 2-octadecanoylamino-3-oxooctadecanoate

生成物 1

HCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate収率 74%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
40 °C

実験手順

Triethylamine (830 mg, 8.20 mmol) and formic acid (227 mg, 4.93 mmol) were added to a chlorobenzene solution (15.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (11.0 mg, 0.03 mmol) and ethyl 2-octadecanoylamino-3-oxooctadecanoate (1.00 g, 1.64 mmol) synthesized in the same method as Example 10. After the reaction mixture was stirred for 3 days at 40° C., water (10 mL) was added thereto and separation operation was carried out at 40° C. to obtain the organic layer. After the organic layer was concentrated until the total amount became 3.11 g, 10 mL of AcOEt was added thereto and recrystallization was carried out to obtain 0.73 g of the title compound (yield: 74%). Anti-form:syn-form was 100:0 and the optical purity of the anti-form was 100% ee.

後処理

  1. customsynthesized in the same method as Example 10
  2. customseparation operation
  3. customwas carried out at 40° C.
  4. customto obtain the organic layer
  5. concentrationAfter the organic layer was concentrated until the total amount
  6. additionwas added
  7. customrecrystallization

出典と根拠

ORDレコード
ord-1258655ab6764efda0d1694134f75ab5
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207370B2

反応ノート

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