Bromomethylcyclopropane → (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid

HRID 1433780Notes

Reaction equation

HRID 1433780 reaction equation
ClC1C=C(I)C=CC=1N.[C:10]([O:14][C:15]([NH:17][C@H:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH:30]2CC2)=[CH:24][CH:23]=1)[C:19]([OH:21])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:33]([O:37]C(N[C@H](C1C=CC(OCCOC2CCCCO2)=CC=1)C(O)=O)=O)([CH3:36])([CH3:35])[CH3:34].C1(CBr)CC1>>[C:10]([O:14][C:15]([NH:17][C@H:18]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:24][CH:23]=1)[C:19]([OH:21])=[O:20])=[O:16])([CH3:12])([CH3:11])[CH3:13]

Participants

5

Reactant 4

HCID 81503BromomethylcyclopropaneHCID 2829302-Chloro-4-iodoanilineHCID 68617730(R)-tert-butoxycarbonylamino-{4-[2-(tetrahydropyran-2-yloxy)-ethoxy]-phenyl}-acetic acidHCID 68618840(R)-tert-butoxycarbonylamino-(4-cyclopropylmethoxy-phenyl)-acetic acid

Product 1

HCID 66815165(R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid

Procedure

Prepared by the same method as described in example 3 except that 2-chloro-4-iodoaniline was used in place of 2-chloro-4-bromoaniline in step 1 and (R)-tert-butoxycarbonylamino-(4-cyclopropylmethoxy-phenyl)-acetic acid was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 2. (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid was prepared by a similar method as described for the preparation of (R)-tert-butoxycarbonylamino-{4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-acetic acid in example 48 except that cyclopropylmethyl bromide was used in place of 2-(2-bromo-ethoxy)-tetrahydropyran.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-a82a85bcf2a7400eafa7e8df296a6c09
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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