Methyl chloroformate → HCID 57092493, compound

HRID 1582355Notes

Reaction equation

HRID 1582355 reaction equation
O1C=CC(NC[C@@H:8]2[O:12][C:11](=[O:13])N(C3C=CC(N4CC[C@H](NC(=O)C)C4)=C(F)C=3)C2)=N1.Cl.[NH2:31][C@@H:32]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][N:49]([C:58]4[CH:62]=[CH:61][O:60][N:59]=4)[C:50]([O:52][CH2:53][C:54]([Cl:57])([Cl:56])[Cl:55])=[O:51])[O:45][C:44]3=[O:63])=[CH:39][C:38]=2[F:64])[CH2:33]1.ClC(OC)=O>>[CH3:8][O:12][C:11]([NH:31][C@@H:32]1[CH2:36][CH2:35][N:34]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][N:49]([C:58]4[CH:62]=[CH:61][O:60][N:59]=4)[C:50]([O:52][CH2:53][C:54]([Cl:57])([Cl:55])[Cl:56])=[O:51])[O:45][C:44]3=[O:63])=[CH:39][C:38]=2[F:64])[CH2:33]1)=[O:13]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 207257105(S)-Isoxazol-3-ylaminomethyl-3-(4-(3(S)-acetamidopyrrolidin-1-yl)-3-fluorophenyl)oxazolidin-2-oneHCID 695848783-(4-(3(r)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(r)-(n-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt

Product 1

HCID 57092493HCID 57092493, compound

Procedure

Using essentially the method for the intermediate of Example 12, starting from 3-(4-(3(R)-aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyloxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (1.61 g, 2.81 mM) and methyl chloroformate gave the desired product (1.61 g). NMR (DMSO-d6) δ: 1.82 (hextet, 1H); 2.11 (hextet, 1H); 3.13 (m, 1H); 3.28 (dd, 1H); 3.39 (dd, 1H); 3.52 (s overlapping m, 4H); 3.82 (dd, 1H); 4.14 (overlapping m, 3H); 4.36 (dd, 1H); 4.97 (d, 1H); 5.03 (m, 1H); 5.08 (d, 1H); 6.72 (t, 1H); 6.89 (d, 1H); 7.08 (dd, 1H); 7.35 (dd, 1H); 7.41 (br, 1H); 8.89 (d, 1H). MS (ESP): 594 (MH+) for C22H23Cl3FN5O7

Sources & evidence

ORD record
ord-6e1887c1d5044d4cbf82ebe42bb817a1
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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