Dichloromethane → (3S)-3-[(Phenylmethoxy)methyl]-1-(phenylmethyl)-2,5-piperazinedione

HRID 1598483Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C@@H:10]([C:19]([OH:21])=O)[NH:11][C:12]([O:14]C(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(Cl)Cl.[CH2:40]([NH:47][CH2:48]C(OCC)=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:40]([N:47]1[CH2:48][C:12](=[O:14])[NH:11][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:19]1=[O:21])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 10868Dicyclohexylcarbodiimide

HCID 80908N-Benzylglycine ethyl ester

HCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 10639705(3S)-3-[(Phenylmethoxy)methyl]-1-(phenylmethyl)-2,5-piperazinedione

Procedure

The title compound was prepared according to the procedure described in Example 2, Step A, except using O-benzyl Boc-L-serine (10 g, 33.8 mmol), dicyclohexylcarbodiimide in methylene chloride (0.5M) (68 mL, 34.0 mmol) and ethyl N-benzylglycinate (6.34 mL, 34.0 mmol). After deprotection with hydrogen chloride in dichloromethane (200 mL), neutralization, and recrystallization of the crude product from ethyl acetate, the title compound was obtained as a white solid (10.3 g). NMR (300 MHz, CDCl3) δ 7.58 (10H, m), 6.41 (1H, br s), 4.74 (1H, d, J=15 Hz), 4.53 (2H, AB q, J=12 Hz, Δν=20 Hz), 4.45 (1H, d, J=15 Hz), 4.22 (1H, m), 3.92 (1H, d, J=17 Hz), 3.88 (1H, dd, J=8, 10 Hz), 3.81 (1H, dd, J=6, 10 Hz), 3.75 (1H, d, J=17 Hz).

Workup

customThe title compound was prepared
customAfter deprotection with hydrogen chloride in dichloromethane (200 mL), neutralization, and recrystallization of the crude product from ethyl acetate

Sources & evidence

ORD record: ord-7ffc4cf8d120404dbc1eecb013279b8d
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05736539

Reaction notes

Loading…