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 1755449ノート

反応式

HRID 1755449 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9af9ebc238734731bec169b762fbf9d5
出典データセット
uspto-grants-2015_10
特許番号
US09169295B2

反応ノート

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