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

HRID 1755444Notes

Reaction equation

HRID 1755444 reaction equation
[NH2:1][C:2](=[O:37])[C@@H:3]([NH:12][C:13](=[O:36])[C@@H:14]([NH:16][C:17](=[O:35])[C@@H:18]([NH:20][C:21](=[O:34])[CH:22]([NH:26][C:27]1[S:28][C:29]([CH:32]=[O:33])=[CH:30][N:31]=1)[CH:23]([CH3:25])[CH3:24])[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:37])[C@@H:3]([NH:12][C:13](=[O:36])[C@@H:14]([NH:16][C:17](=[O:35])[C@@H:18]([NH:20][C:21](=[O:34])[CH:22]([NH:26][C:27]1[S:28][C:29]([CH2:32][OH:33])=[CH:30][N:31]=1)[CH:23]([CH3:24])[CH3:25])[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 86700095N-((S)-1-((S)-1-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-2-(5-formylthiazol-2-ylamino)-3-methylbutanamide

Product 1

HCID 86700094N-((S)-1-((S)-1-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-2-(5-(hydroxymethyl)thiazol-2-ylamino)-3-methylbutanamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of the material from Example 21 (21.5 mg, 0.033 mmol) in EtOH/H2O (4:1) (2.5 mL) is added sodium borohydride (8.35 mg, 0.221 mmol) in 2 portions, separated by ˜5 min and the resulting off white slurry is allowed to stir at room temp for 1.5 h. The reaction is quenched with MeOH (750 μlit) and evaporated to dryness under a gentle stream of N2 to give the title compound that is used directly in the next step. LC/MS (Condition A): ret. T=1.74 min, (M+H)+ 535.

Workup

  1. customseparated by ˜5 min
  2. customThe reaction is quenched with MeOH (750 μlit)
  3. customevaporated to dryness under a gentle stream of N2

Sources & evidence

ORD record
ord-d2fbe40f07a145d9a43bff8e0df3f209
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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