Methoxyacetyl chloride → (R)-tert-Butoxycarbonylamino-[4-(2-methoxy-acetylamino)-phenyl]-acetic acid

HRID 1433755Notes

Reaction equation

HRID 1433755 reaction equation
[C:1]([O:5][C:6](N[C@@H](CC1C=CC(C)=CC=1)C(O)=O)=O)(C)(C)C.[C:21]([O:25][C:26]([NH:28][C@H:29]([C:33]1[CH:38]=[CH:37][C:36](OC[C@H]2COC(C)(C)O2)=[CH:35][CH:34]=1)[C:30]([OH:32])=[O:31])=[O:27])([CH3:24])([CH3:23])[CH3:22].N1([O:57][C:58]([N:62](C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(OC(N[C@H](C1C=CC(OCC(OC)OCC)=CC=1)C(O)=O)=O)(C)(C)C.C(NC1C=CC([C@@](C(OC(C)(C)C)=O)(N)C(O)=O)=CC=1)(=O)C.COCC(Cl)=O>>[C:21]([O:25][C:26]([NH:28][C@H:29]([C:33]1[CH:34]=[CH:35][C:36]([NH:62][C:58](=[O:57])[CH2:1][O:5][CH3:6])=[CH:37][CH:38]=1)[C:30]([OH:32])=[O:31])=[O:27])([CH3:22])([CH3:23])[CH3:24]

Participants

7

Reactant 6

HCID 96623Methoxyacetyl chlorideHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 2761472N-Boc-4-Methyl-L-phenylalanineHCID 67001404(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acidHCID 68620556(R)-(4-acetylamino-phenyl)-tert-butoxycarbonyl-amino-acetic acidHCID 131727731(R)-tert-butoxycarbonylamino-[4-(methoxy-ethoxy-ethoxy)-phenyl]-acetic acid

Product 1

HCID 68618819(R)-tert-Butoxycarbonylamino-[4-(2-methoxy-acetylamino)-phenyl]-acetic acid

Procedure

Prepared by the same method as described in example 1 except that (i) 2-fluoro-4-iodoaniline was used in place of 4-bromoaniline in step 2, (ii) O-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)uronium hexaflurorophosphate was used as the coupling reagent in place of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexaflurorophosphate in step 4, and (iii) (R)-tert-butoxycarbonylamino-[4-(2-methoxy-acetylamino)-phenyl]-acetic acid was used in place of (R)-tert-butyloxycarbonylamino-4-methyoxyphenyl-glycine in step 4. (R)-tert-Butoxycarbonylamino-[4-(2-methoxy-acetylamino)-phenyl]-acetic acid was prepared by the same method as described for preparation of (R)-(4-acetylamino-phenyl)-tert-butoxycarbonyl-amino-acetic acid in example 26 except that methoxy-acetyl chloride was used in place of acetic anhydride in step 5.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-9c3c18bc9be6411e945a3f5b19ff9e29
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

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