Sodium borohydride → N-(2-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-(5-(hydroxymethyl)thiazol-2-ylamino)-3-methylbutanamide

HRID 1755449노트

반응식

HRID 1755449 반응식
[NH2:1][C:2](=[O:31])[C@@H:3]([NH:12][C:13](=[O:30])[CH2:14][NH:15][C:16](=[O:29])[CH:17]([NH:21][C:22]1[S:23][C:24]([CH:27]=[O:28])=[CH:25][N:26]=1)[CH:18]([CH3:20])[CH3:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[BH4-].[Na+]>CCO.O>[NH2:1][C:2](=[O:31])[C@@H:3]([NH:12][C:13](=[O:30])[CH2:14][NH:15][C:16](=[O:29])[CH:17]([NH:21][C:22]1[S:23][C:24]([CH2:27][OH:28])=[CH:25][N:26]=1)[CH:18]([CH3:19])[CH3:20])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86700099N-(2-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-(5-formylthiazol-2-ylamino)-3-methylbutanamide

생성물 1

HCID 86700098N-(2-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-2-oxoethyl)-2-(5-(hydroxymethyl)thiazol-2-ylamino)-3-methylbutanamide

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

To a solution of material from Example 31 in EtOH/H2O (4:1) (2.5 mL) is added sodium borohydride (25.5 mg, 0.674 mmol) in 2 equal portions over 5 min. The resulting light suspension is stirred at room temp for 2 h, quenched with MeOH (3 mL), stirred at room temp for 30 min, quenched with acetone (5 mL), and stirred at room temp for 45 min. All volatiles were evaporated off under a gentle stream of N2 to give the title compound (quantitative yield) that is used in its entirety in the macrocyclization step. LC/MS (Condition A): ret. T=1.45 min, (M+H)+ 450.20.

후처리

  1. customquenched with MeOH (3 mL)
  2. stirringstirred at room temp for 30 min
  3. customquenched with acetone (5 mL)
  4. stirringstirred at room temp for 45 min
  5. customAll volatiles were evaporated off under a gentle stream of N2

출처 및 근거

ORD 기록
ord-9af9ebc238734731bec169b762fbf9d5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169295B2

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