L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → (R)-[4-(2-Azetidin-1-yl-2-oxo-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid

HRID 1433751Notes

Reaction equation

HRID 1433751 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1C=CC=CC=1)C(O)=O)=O)(C)(C)C.[C:20]([O:24][C:25]([NH:27][C@H:28]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C@H:40]2COC(C)(C)[O:41]2)=[CH:34][CH:33]=1)[C:29]([OH:31])=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21].N1(C(=O)CCl)CCC1>>[N:8]1([C:40](=[O:41])[CH2:39][O:38][C:35]2[CH:36]=[CH:37][C:32]([C@@H:28]([NH:27][C:25]([O:24][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:26])[C:29]([OH:31])=[O:30])=[CH:33][CH:34]=2)[CH2:9][CH2:13][CH2:14]1

Participants

4

Reactant 3

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 25431591-(Azetidin-1-yl)-2-chloroethan-1-oneHCID 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid

Product 1

HCID 68620602(R)-[4-(2-Azetidin-1-yl-2-oxo-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid

Procedure

Prepared by the same method as described in example 1 except that (i) 4-iodoaniline was used in place of 4-bromoaniline in step 2 and (ii) (R)-[4-(2-azetidin-1-yl-2-oxo-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid was used in place of (R)-tert-butyloxycarbonylamino-4-methoxyphenylglycine. (R)-[4-(2-Azetidin-1-yl-2-oxo-ethoxy)-phenyl]-tert-butoxycarbonylamino-acetic acid was prepared by a method similar to that used for the preparation of (R)-tert-butyloxycarbonylamino-4-methoxyphenylglycine in example 1 except that 1-azetidin-1-yl-2-chloro-ethanone was used in place of iodomethane.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-e3d9edb56ec84c44958a15bff2328c35
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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