Sodium borohydride → HCID 67170339, compound

HRID 1918308Notes

Reaction equation

C([O:3][C:4]([C:6]1([NH:13][C:14](=[O:34])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][C:25](=[O:33])[C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[BH4-].[Na+]>>[OH:33][CH:25]([C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)[CH2:24][O:23][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH3:22])[C:14]([NH:13][C:6]1([C:4]([OH:5])=[O:3])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:34]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 67168587HCID 67168587, compound

Product 1

HCID 67170339HCID 67170339, compound

Procedure

The compound of step 2 was reduced with sodium borohydride in analogy to step 2 of example 53, the ester intermediate purified by RP HPLC (water/ACN gradient) and hydrolyzed in analogy to step 4 of example 1 to yield the title compound.

Workup

customthe ester intermediate purified by RP HPLC (water/ACN gradient) and hydrolyzed in analogy to step 4 of example 1

Sources & evidence

ORD record: ord-9fc023ccfc05493590a78b1e25974db8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618304B2

Reaction notes

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