L-Serine → HCID 86688741, compound

HRID 1752640Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH2:23][C:24](O)=[O:25])=[C:9]2[CH3:27])=[CH:4][CH:3]=1.[NH2:28][C@@H:29]([CH2:33][OH:34])[C:30]([OH:32])=[O:31]>>[OH:34][CH2:33][C@H:29]([NH:28][C:24](=[O:25])[CH2:23][C:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]=1[CH3:27])[C:30]([OH:32])=[O:31]

Participants

Reactant 2

HCID 5951L-Serine

HCID 56833630HCID 56833630, compound

Product 1

HCID 86688741HCID 86688741, compoundYield 90%

Procedure

Obtained from 6g and (S)-2-amino-3-hydroxypropionic acid similarly to example 28-II, yield 90%, m.p. 120° C. 1H NMR (400 MHz, CDCl3) δ: 7.70 (d, 2H), 7.31 (m, 4H), 7.22 (m, 2H), 6.73 (s broad, 1H), 6.50 (s, 1H), 4.70 (m, 1H), 4.20 (m, 2H), 3.54 (s, 2H), 3.01 (s, 3H), 2.07 (s, 3H).

Sources & evidence

ORD record: ord-08ca59e2f24e45f1abf2adf0507985a8
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09162979B2

Reaction notes

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