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

HRID 1755474Notes

Reaction equation

HRID 1755474 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]([C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]1[S:29][C:30]([CH:33]=[O:34])=[CH:31][N:32]=1)=[O:22])[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]([C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:28]1[S:29][C:30]([CH2:33][OH:34])=[CH:31][N:32]=1)=[O:22])[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 86700119(S)-N-((S)-1-((S)-1-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-1-(5-formylthiazol-2-yl)pyrrolidine-2-carboxamide

Product 1

HCID 86700118(S)-N-((S)-1-((S)-1-((S)-1-Amino-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-yl)-1-(5-(hydroxymethyl)thiazol-2-yl)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Following the procedure as described in Example 32, except using material from Example 81 (6.4 mg, 0.012 mmol), EtOH/H2O (4:1) (3 mL), sodium borohydride (4.2 mg, 0.111 mmol) and stirring at room temp for 2 h, the title compound is isolated (quantitative yield) that is used crude in the next step. LC/MS (Condition A): ret, T=1.54 min, (2M+Na) 1087.51.

Sources & evidence

ORD record
ord-f9462bcaa6cc418e8adca359040e54e4
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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