Sodium borohydride → (S)-N-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-(2-(5-(hydroxymethyl)thiazol-2-ylamino)acetamido)propanamido)propanamide

HRID 1755440Notes

Reaction equation

HRID 1755440 reaction equation
[NH2:1][C:2](=[O:34])[C@@H:3]([NH:12][C:13](=[O:33])[C@@H:14]([NH:16][C:17](=[O:32])[C@@H:18]([NH:20][C:21](=[O:31])[CH2:22][NH:23][C:24]1[S:25][C:26]([CH:29]=[O:30])=[CH:27][N:28]=1)[CH3:19])[CH3:15])[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:34])[C@@H:3]([NH:12][C:13](=[O:33])[C@@H:14]([NH:16][C:17](=[O:32])[C@@H:18]([NH:20][C:21](=[O:31])[CH2:22][NH:23][C:24]1[S:25][C:26]([CH2:29][OH:30])=[CH:27][N:28]=1)[CH3:19])[CH3:15])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86700088(S)-N-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-(2-(5-formylthiazol-2-ylamino)acetamido)propanamido)propanamide

Product 1

HCID 86700089(S)-N-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-(2-(5-(hydroxymethyl)thiazol-2-ylamino)acetamido)propanamido)propanamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a suspension of material from Example 7 (13.2 mg, 0.022 mmol) in EtOH/H2O (4:1) (1.5 mL) is added solid sodium borohydride (7.8 mg, 0.206 mmol) in 2 equal portions over 1 b. After the addition is complete, the reaction is stirred at room temp for 1.5 h and evaporated to dryness to give the title compound (quantitative yield) as a white solid that is used crude in the next step. LC/MS (Condition A): ret. T=0.94-1.16 min, (M+Na) 515.

Workup

  1. additionAfter the addition
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-7b52fcdd6e5a4c97a6f7db490f62860a
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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