Triethylamine → HCID 86741568, compound

HRID 652213Notes

Reaction equation

[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]2[CH2:15][NH:14][C:13]2=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].C(N(CC)CC)C.[C:31]([N:34]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][O:41]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:35]1=[O:61])(=[O:33])[NH2:32]>O1CCCC1>[OH:41][CH2:40][CH2:39][N:36]1[CH2:37][CH2:38][N:34]([C:31]([NH:32][S:18]([NH:21][C:22]([N:14]2[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:13]2=[O:16])=[O:23])(=[O:20])=[O:19])=[O:33])[C:35]1=[O:61]

Participants

Conditions

Temperature: -70 °C

Procedure

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-azetidinone (1.5 g) was suspended in 100 ml of dry tetrahydrofuran and cooled to -70° C. Chlorosulfonylisocyanate (1.1 g) dissolved in 10 ml of dry tetrahydrofuran was dropped in with stirring. The temperature was allowed to rise to 0° C. and maintained there for 20 minutes, followed by cooling to -40° C. Triethylamine (0.9 g) and 2.8 g of 1-carbamoyl-2-oxo-3-[2-[(triphenylmethyl)oxy]ethyl]imidazolidine were added and the mixture was stirred at room temperature for 14 hours. The solvent was removed in vacuo and the work-up procedure of example 34A was followed yielding 4.3 g of (S)-[1-[[[[[[3-(2-hydroxyethyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, potassium salt.

Workup

additionwas dropped in
customto rise to 0° C.
temperaturemaintained there for 20 minutes
temperatureby cooling to -40° C
stirringthe mixture was stirred at room temperature for 14 hours
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-38781c114d5d47ba8371d112b765309f
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04670553

Reaction notes

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