Sodium borohydride → HCID 86700102, compound

HRID 1755453Notes

Reaction equation

HRID 1755453 reaction equation
[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8](=[O:31])[CH2:9][NH:10][C:11](=[O:30])[CH2:12][NH:13][C:14](=[O:29])[C@@H:15]([NH:17][C:18](=[O:28])[CH2:19][NH:20][C:21]2[S:22][C:23]([CH:26]=[O:27])=[CH:24][N:25]=2)[CH3:16])[C@@H:3]1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1.[BH4-].[Na+]>CCO.O>[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8](=[O:31])[CH2:9][NH:10][C:11](=[O:30])[CH2:12][NH:13][C:14](=[O:29])[C@@H:15]([NH:17][C:18](=[O:28])[CH2:19][NH:20][C:21]2[S:22][C:23]([CH2:26][OH:27])=[CH:24][N:25]=2)[CH3:16])[C@@H:3]1[CH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86700103HCID 86700103, compound

Product 1

HCID 86700102HCID 86700102, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Following the procedure as described ion Example 32, except using material from Example 44 (21.4 mg, 0.031 mmol), EtOH/H2O (4:1) (2.0 mL) and sodium borohydride (7.2 mg, 0.190 mmol), the title compound is isolated (quantitative yield) and is used crude, “as is”, in the macrocyclization step. LC/MS (Condition A): ret. T=1.90 min, (M+Na) 601.29.

Sources & evidence

ORD record
ord-ca22b0a1e3ea4b7a8f51e57a133df2d8
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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