Methyl iodide → methyl (2RS,3S)-3-amino-2-hydroxyheptanoate

HRID 1953441Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]([OH:14])[C:4]([O:6][CH2:7]C1C=CC=CC=1)=[O:5].C(Br)C1C=CC=CC=1.CI>>[NH2:1][C@@H:2]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]([OH:14])[C:4]([O:6][CH3:7])=[O:5]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 7498Benzyl Bromide

HCID 56995658phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate

Product 1

HCID 54272153methyl (2RS,3S)-3-amino-2-hydroxyheptanoateYield 91%

Procedure

The same reaction procedure for synthesizing of phenylmethyl (2RS,3S)-3-amino-2-hydroxyheptanoate as in Reference Example 17 was repeated except that benzyl bromide used in Reference Example 17 was replaced by 579 mg of methyl iodide, whereby 683 mg of the captioned methyl (2RS,3S)-3-amino-2-hydroxyheptanoate was obtained in a yield of 91%.

Workup

customThe same reaction procedure

Sources & evidence

ORD record: ord-c5f9c186745040cf8ede17d73f1edc76
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06117870

Reaction notes

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