tert-butyl (2S,4R)-2-[(4-amino-2-methoxyphenoxy)methyl]4-hydroxypyrrolidine-1-carboxylate → tert-butyl (2S,4R)-2-({4-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-methoxyphenoxy}methyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 1181365노트

반응식

HRID 1181365 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.NC1[CH:43]=[CH:42][C:26]([O:27][CH2:28][C@@H:29]2[CH2:33][C@@H:32]([OH:34])[CH2:31][N:30]2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[C:25]([O:44][CH3:45])[CH:24]=1>C1(O)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([C:21]4[CH:43]=[CH:42][C:26]([O:27][CH2:28][C@@H:29]5[CH2:33][C@@H:32]([OH:34])[CH2:31][N:30]5[C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])=[C:25]([O:44][CH3:45])[CH:24]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 86594898tert-butyl (2S,4R)-2-[(4-amino-2-methoxyphenoxy)methyl]4-hydroxypyrrolidine-1-carboxylateHCID 178499302HCID 178499302, 화합물

생성물 1

HCID 86594897tert-butyl (2S,4R)-2-({4-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-methoxyphenoxy}methyl)-4-hydroxypyrrolidine-1-carboxylate수율 41.8%

시약·촉매·용매 1

HCID 996Phenol용매

실험 절차

Methyl 5-(4-chlorophenyl)-3-{[(E)-(dimethylamino)methylidene]amino}-2-thiophenecarboxylate (857 mg, 2.66 mmol) was mixed with tert-butyl (2S,4R)-2-[(4-amino-2-methoxyphenoxy)methyl]4-hydroxypyrrolidine-1-carboxylate (900 mg) in phenol (1.0 g) at 120° C. for 15 min. Workup and purification of the reaction mixture provided 650 mg of tert-butyl (2S,4R)-2-({4-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-methoxyphenoxy}methyl)-4-hydroxypyrrolidine-1-carboxylate. A portion of this material (105 mg, 0.179 mmol) was dissolved in a 1:1 mixture of dichloromethane and trifluoroacetic acid. The mixture was stirred at room temperature for 10 min and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated solution of NaHCO3, brine, dried (Na2SO4) and concentrated to provide the title compound.

후처리

  1. customWorkup and purification of the reaction mixture

출처 및 근거

ORD 기록
ord-1bf348c52b264122bafe87d96cc4cc9b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285557B2

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