Acetic Acid → HCID 20197302, 화합물

반응식

O([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]([OH:26])=O)[CH:22]=2)[NH:17][CH:16]=1)=[O:11])C1C=CC=CC=1.C(N1[CH:38]=[CH:37]N=C1)(N1C=CN=C1)=O.[BH4-].[Li+].C(O)(=O)C.O1[CH2:49][CH2:48][CH2:47][CH2:46]1>>[C:38]1([CH2:8][O:9][C:10](=[O:11])[NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][OH:26])[CH:22]=3)[NH:17][CH:16]=2)[CH:37]=[CH:49][CH:48]=[CH:47][CH:46]=1

참가 물질

반응물 5

HCID 176Acetic Acid

HCID 8028Tetrahydrofuran2회

HCID 682631,1'-Carbonyldiimidazole

HCID 4148881Lithium borohydride

HCID 20197295HCID 20197295, 화합물

생성물 1

HCID 20197302HCID 20197302, 화합물

실험 절차

A solution of 3-[2-[[(phenoxymethoxy)carbonyl]amino]ethyl]-1H-indole-5-carboxylic acid (9 g) and carbonyldiimidazole (5.2 g) in dry tetrahydrofuran (THF) (150 ml) was stirred vigorously under nitrogen at room temperature for 5 h. A solution of lithium borohydride (1.6 g) in dry THF (70 ml) was added over 70 min and the mixture then stirred for 18 h. Aqueous acetic acid (30%, 25 ml) was added slowly to the ice-cooled mixture and the solution was then partitioned between brine (25%, 300 ml) and ethyl acetate (250 ml). The organic layer was washed with sulphuric acid (0.4M, saturated with sodium chloride, 3×80 ml), brine (100 ml) and potassium carbonate solution (25%, 2×100 ml). The dried (MgSO4) solution was evaporated in vacuo, the residue taken up in dichloromethane (150 ml) and insoluble material was filtered off. The filtrate was evaporated in vacuo to leave the alcohol (9 g) as a colourless oil containing some (ca. 45 mole %) ethyl acetate.