1-Hydroxybenzotriazole → methyl 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-3-yl)-6-oxohexanoate

HRID 732628ノート

反応式

HRID 732628 の反応式
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:23]1([C@H:33]([N:35]([CH2:43][C@@H:44]2[C@@H:48]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:47][NH:46][CH2:45]2)[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.[C:55]([O:64][CH3:65])(=[O:63])[CH2:56][CH2:57][CH2:58][CH2:59][C:60]([O-])=[O:61]>ClCCl.C(N(CC)CC)C>[C:38]([O:37][C:36]([N:35]([CH2:43][C@@:44]1([C:60](=[O:61])[CH2:59][CH2:58][CH2:57][CH2:56][C:55]([O:64][CH3:65])=[O:63])[C@H:48]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH2:47][NH:46][CH2:45]1)[C@@H:33]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:34])=[O:42])([CH3:40])([CH3:41])[CH3:39]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6994472Methyl adipateHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate

生成物 1

HCID 68910563methyl 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-3-yl)-6-oxohexanoate収率 94.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

At room temperature, 144 mg of WSC hydrochloride, 101 mg of HOBt, 215 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate and 0.08 ml of triethylamine were added in that order to a mixture of 80 mg of monomethyl adipate and 5 ml of dichloromethane and stirred for 3 days, and then the reaction was quenched by adding water, and this was extracted with chloroform and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 270 mg of methyl 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-3-yl)-6-oxohexanoate as a colorless amorphous substance. FP: 573.

後処理

  1. customthe reaction was quenched
  2. additionby adding water
  3. extractionthis was extracted with chloroform
  4. washwashed with saturated brine
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

出典と根拠

ORDレコード
ord-00962627a1714f879a9340bd89d80212
出典データセット
uspto-grants-2009_09
特許番号
US07585886B2

反応ノート

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