Hydrochloric Acid → (R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid

HRID 47149

反応式

HRID 47149 の反応式
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17].Cl>O.O1CCCC1>[CH3:19][O:18][C:16]([NH:1][C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([OH:12])=[O:11])=[O:17]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide2 回HCID 71567D-Phenylalanine

生成物 1

HCID 10799103(R)-2-(methoxycarbonylamino)-3-phenylpropanoic acid収率 113.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of D-phenylalanine (25.00 g, 0.151 mol) and sodium hydroxide (6.05 g, 0.151 mol) in water (170 ml) and tetrahydrofuran (225 ml) was cooled to −15° C., and a solution of methyl chloroformate (18.6 g, 0.197 mol) in tetrahydrofuran (50 ml) was added dropwise. When the addition was ˜half complete, a solution of sodium hydroxide (9.10 g, 0.227 mol) in water (20 ml) was also added dropwise. When the additions were complete, the mixture was stirred at room temperature for an additional 2 hours and acid fixed with 10% hydrochloric acid. The acid was extracted twice with diethylether, and the extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a clear oil (38.38 g). HPLC 6.01 min (78.9%), 7.32 min (5.0%), 8.29 min (10.8%), 8.42 min (0.5%), 9.95 min (1.2%), 10.27 min (2.8%), 11.92 min (0.7%).

後処理

  1. additionWhen the addition
  2. additionwas also added dropwise
  3. extractionThe acid was extracted twice with diethylether
  4. washthe extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-a3c6958a412c4737b0184493e43e5a7a
出典データセット
uspto-grants-2004_03
特許番号
USRE038452E1

関連ノート

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